Towards the total synthesis of vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A

Brett D. Schwartz; David P. Tilly; Ralf Heim; Stefan Wiedemann; Craig M. Williams; Paul V. Bernhardt

doi:10.1002/ejoc.200600246

Towards the total synthesis of vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A

Brett D. Schwartz, David P. Tilly, Ralf Heim, Stefan Wiedemann, Craig M. Williams^*, Paul V. Bernhardt

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

Abstract

Studies detailing synthetic approaches to a variety of biosynthetically related vibsanin-type diterpenes (i.e. vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxy-vibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A) are discussed. Biogenetically modelled approaches are coupled with an investigation of classical and modern six- to seven-membered ring-expansion protocols, which gain access to the central core of these natural products.

Original language	English
Pages (from-to)	3181-3192
Number of pages	12
Journal	European Journal of Organic Chemistry
Issue number	14
DOIs	https://doi.org/10.1002/ejoc.200600246
Publication status	Published - 10 Jul 2006
Externally published	Yes

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title = "Towards the total synthesis of vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A",

abstract = "Studies detailing synthetic approaches to a variety of biosynthetically related vibsanin-type diterpenes (i.e. vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxy-vibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A) are discussed. Biogenetically modelled approaches are coupled with an investigation of classical and modern six- to seven-membered ring-expansion protocols, which gain access to the central core of these natural products.",

keywords = "Diterpenes, Natural products, Ring expansion, Terpenoids, Vibsanin",

author = "Schwartz, \{Brett D.\} and Tilly, \{David P.\} and Ralf Heim and Stefan Wiedemann and Williams, \{Craig M.\} and Bernhardt, \{Paul V.\}",

year = "2006",

month = jul,

day = "10",

doi = "10.1002/ejoc.200600246",

language = "English",

pages = "3181--3192",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag GmbH",

number = "14",

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TY - JOUR

T1 - Towards the total synthesis of vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A

AU - Schwartz, Brett D.

AU - Tilly, David P.

AU - Heim, Ralf

AU - Wiedemann, Stefan

AU - Williams, Craig M.

AU - Bernhardt, Paul V.

PY - 2006/7/10

Y1 - 2006/7/10

N2 - Studies detailing synthetic approaches to a variety of biosynthetically related vibsanin-type diterpenes (i.e. vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxy-vibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A) are discussed. Biogenetically modelled approaches are coupled with an investigation of classical and modern six- to seven-membered ring-expansion protocols, which gain access to the central core of these natural products.

AB - Studies detailing synthetic approaches to a variety of biosynthetically related vibsanin-type diterpenes (i.e. vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxy-vibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A) are discussed. Biogenetically modelled approaches are coupled with an investigation of classical and modern six- to seven-membered ring-expansion protocols, which gain access to the central core of these natural products.

KW - Diterpenes

KW - Natural products

KW - Ring expansion

KW - Terpenoids

KW - Vibsanin

UR - https://www.scopus.com/pages/publications/33746098889

U2 - 10.1002/ejoc.200600246

DO - 10.1002/ejoc.200600246

M3 - Article

SN - 1434-193X

SP - 3181

EP - 3192

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 14

ER -

Towards the total synthesis of vibsanin E, 15-O-methylcyclovibsanin B, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A

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