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Volume No. 6 2010 No. 1 - 79 Pages 699 - 1245

Table of Contents

107

Full Research Paper

Review

Letter

Preliminary Communication

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Brønsted acid-promoted azide–olefin [3 + 2] cycloadditions for the preparation of contiguous aminopolyols: The importance of disiloxane ring size to a diastereoselective, bidirectional approach to zwittermicin A

Hubert Muchalski,
Ki Bum Hong and
Jeffrey N. Johnston

Beilstein J. Org. Chem. 2010, 6, 1206–1210, doi:10.3762/bjoc.6.138

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Scheme 1: Retrosynthetic analysis outlining the stereocontrolled construction of the aminopolyol core of (−)-...

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Scheme 2: Depictions of the likely major conformations of the siloxane (A) and disiloxane (B) rings.

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Scheme 3: Confirmation of the relative stereochemistry of bis(triazoline) 14a. (a) TfOH, CH₃CN, rt, 18 h; (b)...

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Letter

Published 20 Dec 2010

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Anthracene appended pyridinium amide–urea conjugate in selective fluorometric sensing of L-N-acetylvaline salt

Kumaresh Ghosh,
Tanmay Sarkar and
Asoke P. Chattopadhyay

Beilstein J. Org. Chem. 2010, 6, 1211–1218, doi:10.3762/bjoc.6.139

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Figure 1: Synthesized compounds 1 and 2.

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Scheme 1: Syntheses of 1 and 2.

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Figure 2: Change in ¹H NMR of (A) 1 (400 MHz, CDCl₃ containing 0.4% d₆-DMSO; c = 2.80 × 10⁻³ M) and in the pr...

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Figure 3: Change in fluorescence ratio of 1 upon addition of one equivalent of anions (c = 4.31 × 10⁻⁵ M) at ...

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Figure 4: Change in emission of 1 (c = 4.31 × 10⁻⁵ M) upon gradual addition of tetrabutylammonium salts of (a...

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Figure 5: Suggested modes of binding of the amino acid salts into the open cleft of 1.

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Figure 6: Fluorescence titration curves for 1 (c = 4.31 × 10⁻⁵ M) at 492 nm.

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Figure 7: Fluorescence decays (at λ_max = 420 nm) of receptor 1 upon the addition of 1 equiv of L-N-acetylvali...

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Figure 8: Change in absorbance of 1 (c = 4.31 × 10⁻⁵ M) upon gradual addition of tetrabutylammonium salts of ...

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Figure 9: DFT optimized geometry of the complex of 1 with L-N-acetylvaline carboxylate salt [a = 1.93 Å, b = ...

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Letter

Published 21 Dec 2010

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The allylic chalcogen effect in olefin metathesis

Yuya A. Lin and
Benjamin G. Davis

Beilstein J. Org. Chem. 2010, 6, 1219–1228, doi:10.3762/bjoc.6.140

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Scheme 1: a) Variation of olefin metathesis: CM = cross-metathesis; RCM = ring-closing metathesis; ROM = ring...

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Figure 1: Allylic hydroxy activation in RCM [19].

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Figure 2: Possible complexes generated through preassociation of allylic alcohol with ruthenium.

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Scheme 2: The influence of different OR groups on ring size-selectivity [21].

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Scheme 3: Synthesis of palmerolide A precursors by Nicolaou et al. illustrates enhancement by an allylic hydr...

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Scheme 4: a) Acceleration of ring-closing enyne metathesis by the allylic hydroxy group [23]. b) Proposed mode of...

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Scheme 5: a) Effect of the hydroxy group on the rate and steroselectivity of ROCM [24]. b) Proposed H-bonded ruth...

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Scheme 6: Plausible explanation for chemoselective CM of diene 16 [25].

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Scheme 7: a) Efficient cross-metathesis of S-allylcysteine [17]. b) Comparison of relative reactivity between all...

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Scheme 8: a) Macrocycle synthesis by carbonyl-relayed RCM. b) Putative complex in carbonyl-relayed RCM [33].

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Scheme 9: a) Sulfur assisted cross-metathesis [17]. b) Putative unproductive chelates for larger ring sizes gener...

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Scheme 10: Functionalization of Mukaiyama aldol product by CM in aqueous media [37].

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Scheme 11: Comparison of reactivity between allyl sulfides and allyl selenides in aqueous cross-metathesis [38].

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Scheme 12: Ring-closing metathesis on a protein [18].

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Scheme 13: Expanded substrate scope of cross-metathesis on proteins [38].

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Review

Published 23 Dec 2010

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Highly substituted benzannulated cyclooctanol derivatives by samarium diiodide-induced cyclizations

Jakub Saadi,
Irene Brüdgam and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2010, 6, 1229–1245, doi:10.3762/bjoc.6.141

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Scheme 1: SmI₂-induced cyclizations of styryl-substituted γ-ketoesters A to benzannulated cyclooctanol deriva...

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Scheme 2: Three-step synthesis of precursor 4 starting from siloxycyclopropane derivative 1.

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Scheme 3: Attempted cyclizations of diastereomeric cycloheptanone derivatives 5a and 5b.

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Scheme 4: Samarium diiodide-induced cyclization of γ-ketoester 7a to tricyclic compound 8.

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Scheme 5: Samarium diiodide-induced cyclizations of methyl ketone 4 and iso-propyl ketone 11.

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Figure 1: NOESY-correlation for compound 10.

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Figure 2: NOESY-correlation for compound 9.

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Scheme 6: Assumed transition structures and intermediates A, B, or C for the cyclizations of (2-propenyl)phen...

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Scheme 7: Reductive fragmentation of highly hindered ketoester 14.

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Scheme 8: Samarium diiodide-induced cyclization of phenyl-substituted substrate 16 leading to lactones 17a an...

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Figure 3: Molecular structure (Diamond [52]) of compound 17b.

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Scheme 9: Samarium diiodide-induced cyclizations of (E)-(1-propenyl)phenyl-substituted γ-ketoesters 18, 21, a...

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Figure 4: Proposed transition structure for the cyclization of (E)-1-propenyl-substituted substrates (HMPA li...

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Scheme 10: Attempted samarium diiodide-induced cyclizations with (E)-1-propenyl-substituted precursors 26a and ...

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Scheme 11: Attempted samarium diiodide-induced cyclization of (Z)-1-propenyl-substituted precursor 30.

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Scheme 12: Samarium diiodide-induced cyclizations of γ-ketoesters 33 and 36.

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Scheme 13: Samarium diiodide-induced cyclizations of diastereomeric stilbenyl-substituted γ-ketoesters 38a and ...

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Figure 5: Molecular structure (Diamond [52]) of compound 40.

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Scheme 14: Attempted cyclization of β-dialkyl-substituted styrene derivative 41.

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Scheme 15: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of α-styryl-substituted γ-ke...

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Scheme 16: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of β-styryl-substituted γ-ke...

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Full Research Paper

Published 28 Dec 2010

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