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2 article(s) from Scheeff, Stephan

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

Stephan Scheeff and
Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

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Scheme 1: Molecular structures of the archazolids.

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Scheme 2: Retrosynthetic analysis of archazolid A by the Menche group.

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Scheme 3: Synthesis of north-eastern fragment 5 through a Paterson anti-aldol addition and multiple Still–Gen...

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Scheme 4: Synthesis of 4 through an Abiko–Masamune anti-aldol addition.

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Scheme 5: Thiazol construction and synthesis of the southern fragment 6.

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Scheme 6: Completion of the total synthesis of archazolid A.

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Scheme 7: Synthesis of archazolid B (2) by a ring closing Heck reaction of 38.

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Scheme 8: Retrosynthetic analysis of archazolid B by the Trauner group.

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Scheme 9: Synthesis of acid 40 from Roche ester 41 involving a highly efficient Trost–Alder ene reaction.

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Scheme 10: Synthesis of precursor 39 for the projected relay RCM reaction.

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Scheme 11: Final steps of Trauner’s total synthesis of archazolid B.

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Scheme 12: Overview of the different retrosynthetic approaches for the synthesis of dihydroarchazolid B (3) re...

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Scheme 13: Fragment synthesis of 69 towards the total synthesis of 3.

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Scheme 14: Organometallic addition of the side chain to access free alcohol 75.

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Review

Published 07 Jun 2017

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Modular synthesis of the pyrimidine core of the manzacidins by divergent Tsuji–Trost coupling

Sebastian Bretzke,
Stephan Scheeff,
Felicitas Vollmeyer,
Friederike Eberhagen,
Frank Rominger and
Dirk Menche

Beilstein J. Org. Chem. 2016, 12, 1111–1121, doi:10.3762/bjoc.12.107

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Figure 1: Modular concept for manzacidin synthesis based on a Tsuji–Trost coupling of joint intermediate 5.

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Scheme 1: General concept for heterocycles synthesis based on a nucleophilic addition and Tsuji–Trost couplin...

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Scheme 2: Synthesis of homoallylic alcohol 12 by multi-component reactions.

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Scheme 3: Preparation of urea-type cyclization precursor 19.

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Scheme 4: Stereodivergent synthesis of 1,3-syn- and anti-tetrahydropyrimidinones [31].

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Scheme 5: Stereoselective synthesis of all possible stereoisomers of the manzacidin core amine by asymmetric ...

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Scheme 6: Synthesis of the authentic cyclization precursor 5.

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Figure 2: X-ray structure of 39.

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Scheme 7: Divergent Tsuji–Trost coupling and completion of the synthesis of authentic pyrimidinones 3 and 4.

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Full Research Paper

Published 02 Jun 2016

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