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2 article(s) from Stark, Christian B W

The direct oxidative diene cyclization and related reactions in natural product synthesis

Juliane Adrian,
Leona J. Gross and
Christian B. W. Stark

Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200

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Graphical Abstract

Scheme 1: Putative structures of geraniol 1a (R = H) or 1b (R = H) (in 1924), their expected dihydroxylation ...

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Scheme 2: Correlation between the substrate double bond geometry and relative stereochemistry of the correspo...

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Scheme 3: Mechanisms and classification for the metal-mediated oxidative cyclizations to form 2,5-disubstitut...

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Scheme 4: Synthesis of (+)-anhydro-D-glucitol and (+)-D-chitaric acid using an OsO₄-mediated oxidative cycliz...

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Scheme 5: Total synthesis of neodysiherbaine A via a Ru(VIII)- and an Os(VI)-catalyzed oxidative cyclization,...

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Scheme 6: Formal synthesis of ionomycin by Kocienski and co-workers.

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Scheme 7: Total synthesis of amphidinolide F by Fürstner and co-workers.

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Scheme 8: Brown`s and Donohoe`s oxidative cyclization approach to cis-solamin A.

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Scheme 9: Total synthesis of cis-solamin A using a Ru(VIII)-catalyzed oxidative cyclization and enzymatic des...

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Scheme 10: Donohoe´s double oxidative cyclization approach to cis-sylvaticin.

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Scheme 11: Permanganate-mediated approach to cis-sylvaticin by Brown and co-workers.

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Scheme 12: Total synthesis of membranacin using a KMnO₄-mediated oxidative cyclization.

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Scheme 13: Total synthesis of membrarollin and its analogue 21,22-diepi-membrarollin.

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Scheme 14: Total synthesis of rollidecin C and D using a late stage Re(VII)-catalyzed oxidative polycyclizatio...

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Scheme 15: Co(II)-catalyzed oxidative cyclization in the total synthesis of asimilobin and gigantetrocin A.

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Scheme 16: Mn(VII)-catalyzed oxidative cyclization of a 1,5-diene in the synthesis of trans-(+)-linalool oxide....

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Scheme 17: Re(VII)-catalyzed oxidative cyclization in the total synthesis of teurilene.

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Scheme 18: Total synthesis of (+)-eurylene via Re(VII)- and Cr(VI)-mediated oxidative cyclizations.

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Scheme 19: Synthesis of cis- and trans-THF Rings of eurylene via Mn(VII)-mediated oxidative cyclizations.

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Scheme 20: Cr(VI)-catalyzed oxidative cyclization in the total synthesis of venustatriol by Corey et al.

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Scheme 21: Ru(VIII)-catalyzed oxidative cyclization of a 1,5-diene in the synthesis and evaluation of its ster...

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Scheme 22: Ru(VII)-catalyzed oxidative cyclization of a 5,6-dihydroxy alkene in the synthesis of the core stru...

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Review

Published 30 Sep 2016

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Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

Jens Schmidt,
Zeinab Khalil,
Robert J. Capon and
Christian B. W. Stark

Beilstein J. Org. Chem. 2014, 10, 1228–1232, doi:10.3762/bjoc.10.121

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Figure 1: Known heronapyrroles A–C and nitropyrrolins A–E.

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Scheme 1: Plausible biosynthesis of heronapyrroles A–D.

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Scheme 2: Synthesis of heronapyrrole D.

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Letter

Published 26 May 2014

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