Total synthesis of (-)-heliespirone a and (+)-heliespirone C

Philip Norcott; Christopher S.P. McErlean

doi:10.1002/ejoc.201402420

Total synthesis of (-)-heliespirone a and (+)-heliespirone C

Philip Norcott, Christopher S.P. McErlean^*

^*Corresponding author for this work

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

3 Citations (Scopus)

Abstract

Total syntheses of the spiro-epimeric natural products (-)-heliespirone A and (+)-heliespirone C are described. The successful strategy involved an aromatic Claisen rearrangement, a diastereoselective Sharpless asymmetric dihydroxylation (AD) reaction, and an intramolecular oxa-Michael addition.

Original language	English
Pages (from-to)	5056-5062
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	23
DOIs	https://doi.org/10.1002/ejoc.201402420
Publication status	Published - Aug 2014
Externally published	Yes

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title = "Total synthesis of (-)-heliespirone a and (+)-heliespirone C",

abstract = "Total syntheses of the spiro-epimeric natural products (-)-heliespirone A and (+)-heliespirone C are described. The successful strategy involved an aromatic Claisen rearrangement, a diastereoselective Sharpless asymmetric dihydroxylation (AD) reaction, and an intramolecular oxa-Michael addition.",

keywords = "Asymmetric synthesis, Michael addition, Natural products, Sigmatropic rearrangement, Spiro compounds, Total synthesis",

author = "Philip Norcott and McErlean, {Christopher S.P.}",

year = "2014",

month = aug,

doi = "10.1002/ejoc.201402420",

language = "English",

volume = "2014",

pages = "5056--5062",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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AU - Norcott, Philip

AU - McErlean, Christopher S.P.

PY - 2014/8

Y1 - 2014/8

N2 - Total syntheses of the spiro-epimeric natural products (-)-heliespirone A and (+)-heliespirone C are described. The successful strategy involved an aromatic Claisen rearrangement, a diastereoselective Sharpless asymmetric dihydroxylation (AD) reaction, and an intramolecular oxa-Michael addition.

AB - Total syntheses of the spiro-epimeric natural products (-)-heliespirone A and (+)-heliespirone C are described. The successful strategy involved an aromatic Claisen rearrangement, a diastereoselective Sharpless asymmetric dihydroxylation (AD) reaction, and an intramolecular oxa-Michael addition.

KW - Asymmetric synthesis

KW - Michael addition

KW - Natural products

KW - Sigmatropic rearrangement

KW - Spiro compounds

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84905572301&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201402420

DO - 10.1002/ejoc.201402420

M3 - Article

SN - 1434-193X

VL - 2014

SP - 5056

EP - 5062

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 23

ER -

Total synthesis of (-)-heliespirone a and (+)-heliespirone C

Abstract

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