Total Synthesis of (−)-Teucvidin

Xiaozu Liu; Chi Sing Lee

doi:10.1021/ol301098s

Total Synthesis of (−)-Teucvidin

Xiaozu Liu
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

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

37 Citations (Scopus)

Abstract

A concise enantioselective synthesis of (−)-teucvidin has been achieved. Our synthetic strategy involved the diastereoselective Michael/Conia–ene cascade cyclization reaction for rapid establishment of the cis-decalin skeleton with three new stereogenic centers in one pot (72%, single diastereomer), the epoxidation/dealkoxycarbonylation protocol for construction of the fused furanone moiety, and the O-allylation/Claisen rearrangement protocol for construction of the all-carbon quaternary center at C9 of the clerodane skeleton.

Original language	English
Pages (from-to)	2886-2889
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	11
Early online date	17 May 2012
DOIs	https://doi.org/10.1021/ol301098s
Publication status	Published - 1 Jun 2012

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title = "Total Synthesis of (−)-Teucvidin",

abstract = "A concise enantioselective synthesis of (−)-teucvidin has been achieved. Our synthetic strategy involved the diastereoselective Michael/Conia–ene cascade cyclization reaction for rapid establishment of the cis-decalin skeleton with three new stereogenic centers in one pot (72\%, single diastereomer), the epoxidation/dealkoxycarbonylation protocol for construction of the fused furanone moiety, and the O-allylation/Claisen rearrangement protocol for construction of the all-carbon quaternary center at C9 of the clerodane skeleton.",

author = "Xiaozu Liu and Lee, \{Chi Sing\}",

note = "This work is supported by the National Natural Science Foundation of China (Grant Nos. 20672003 and 20972004) and the Peking University Shenzhen Graduate School. Publisher Copyright: {\textcopyright} 2012 American Chemical Society",

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doi = "10.1021/ol301098s",

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T1 - Total Synthesis of (−)-Teucvidin

AU - Liu, Xiaozu

AU - Lee, Chi Sing

N1 - This work is supported by the National Natural Science Foundation of China (Grant Nos. 20672003 and 20972004) and the Peking University Shenzhen Graduate School. Publisher Copyright: © 2012 American Chemical Society

PY - 2012/6/1

Y1 - 2012/6/1

N2 - A concise enantioselective synthesis of (−)-teucvidin has been achieved. Our synthetic strategy involved the diastereoselective Michael/Conia–ene cascade cyclization reaction for rapid establishment of the cis-decalin skeleton with three new stereogenic centers in one pot (72%, single diastereomer), the epoxidation/dealkoxycarbonylation protocol for construction of the fused furanone moiety, and the O-allylation/Claisen rearrangement protocol for construction of the all-carbon quaternary center at C9 of the clerodane skeleton.

AB - A concise enantioselective synthesis of (−)-teucvidin has been achieved. Our synthetic strategy involved the diastereoselective Michael/Conia–ene cascade cyclization reaction for rapid establishment of the cis-decalin skeleton with three new stereogenic centers in one pot (72%, single diastereomer), the epoxidation/dealkoxycarbonylation protocol for construction of the fused furanone moiety, and the O-allylation/Claisen rearrangement protocol for construction of the all-carbon quaternary center at C9 of the clerodane skeleton.

U2 - 10.1021/ol301098s

DO - 10.1021/ol301098s

M3 - Letter

SN - 1523-7060

VL - 14

SP - 2886

EP - 2889

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Total Synthesis of (−)-Teucvidin

Abstract

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