Total Synthesis of (-)-Blepharocalyxin D and Analogues

Benjamin D. Cons; Adam J. Bunt; Christopher D. Bailey; Christine L. Willis

doi:10.1021/ol400736w

Total Synthesis of (-)-Blepharocalyxin D and Analogues

Benjamin D. Cons, Adam J. Bunt, Christopher D. Bailey, Christine L. Willis^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

49 Citations (Scopus)

Abstract

An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with gamma,delta-unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.

Original language	English
Pages (from-to)	2046-2049
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	8
DOIs	https://doi.org/10.1021/ol400736w
Publication status	Published - 19 Apr 2013

Research Groups and Themes

Organic & Biological

Keywords

BLEPHAROCALYXINS C-E
STEREOSELECTIVE-SYNTHESIS
ALPINIA-BLEPHAROCALYX
PRINS-CYCLIZATION
ENOL ETHERS
DIARYLHEPTANOIDS
SEEDS
TETRAHYDROPYRANS
DERIVATIVES

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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research

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@article{ec1d1da28dbf4e5bb524cba89a0ad5b7,

title = "Total Synthesis of (-)-Blepharocalyxin D and Analogues",

abstract = "An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with gamma,delta-unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.",

keywords = "BLEPHAROCALYXINS C-E, STEREOSELECTIVE-SYNTHESIS, ALPINIA-BLEPHAROCALYX, PRINS-CYCLIZATION, ENOL ETHERS, DIARYLHEPTANOIDS, SEEDS, TETRAHYDROPYRANS, DERIVATIVES",

author = "Cons, \{Benjamin D.\} and Bunt, \{Adam J.\} and Bailey, \{Christopher D.\} and Willis, \{Christine L.\}",

year = "2013",

month = apr,

day = "19",

doi = "10.1021/ol400736w",

language = "English",

volume = "15",

pages = "2046--2049",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Total Synthesis of (-)-Blepharocalyxin D and Analogues

AU - Cons, Benjamin D.

AU - Bunt, Adam J.

AU - Bailey, Christopher D.

AU - Willis, Christine L.

PY - 2013/4/19

Y1 - 2013/4/19

N2 - An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with gamma,delta-unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.

AB - An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with gamma,delta-unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.

KW - BLEPHAROCALYXINS C-E

KW - STEREOSELECTIVE-SYNTHESIS

KW - ALPINIA-BLEPHAROCALYX

KW - PRINS-CYCLIZATION

KW - ENOL ETHERS

KW - DIARYLHEPTANOIDS

KW - SEEDS

KW - TETRAHYDROPYRANS

KW - DERIVATIVES

U2 - 10.1021/ol400736w

DO - 10.1021/ol400736w

M3 - Article (Academic Journal)

C2 - 23560679

SN - 1523-7060

VL - 15

SP - 2046

EP - 2049

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Total Synthesis of (-)-Blepharocalyxin D and Analogues

Abstract

Research Groups and Themes

Keywords

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3-month Core Capability for Chemistry Research

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