A Biomimetic Synthesis of (±)-Basiliolide B

Long Min; Yang Zhang; Xuefeng Liang; Junrong Huang; Wenli Bao; Chi Sing Lee

doi:10.1002/anie.201405770

A Biomimetic Synthesis of (±)-Basiliolide B

Long Min
, Yang Zhang
, Xuefeng Liang
, Junrong Huang
, Wenli Bao
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

21 Citations (Scopus)

Abstract

A highly diastereoselective and practical biomimetic total synthesis of (±)-basiliolide B has been achieved through the study of the two proposed biosynthetic pathways (O-methylation and O-acylation) for the unprecedented 7-methoxy-4,5-dihydro-3H-oxepin-2-one (C ring). The synthesis featured a cyclopropanation/ring opening strategy for establishing the stereogenic centers at C8 and C9, a biomimetic 2-pyrone Diels–Alder cycloaddition for the synthesis of the ABD ring system, and finally a highly efficient biomimetic intramolecular O-acylation for the C ring formation. This result provides an important perspective on the biosynthetic origin of the unprecedented 7-membered acyl ketene acetal moiety of the C ring.

Original language	English
Pages (from-to)	11294-11297
Number of pages	4
Journal	Angewandte Chemie. International Edition
Volume	53
Issue number	42
Early online date	27 Aug 2014
DOIs	https://doi.org/10.1002/anie.201405770
Publication status	Published - 13 Oct 2014

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This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 9 Industry, Innovation, and Infrastructure

User-Defined Keywords

Diels–Alder reaction
basiliolide B
biomimetic synthesis
cyclopropanation
O-acylation

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10.1002/anie.201405770

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title = "A Biomimetic Synthesis of (±)-Basiliolide B",

abstract = "A highly diastereoselective and practical biomimetic total synthesis of (±)-basiliolide B has been achieved through the study of the two proposed biosynthetic pathways (O-methylation and O-acylation) for the unprecedented 7-methoxy-4,5-dihydro-3H-oxepin-2-one (C ring). The synthesis featured a cyclopropanation/ring opening strategy for establishing the stereogenic centers at C8 and C9, a biomimetic 2-pyrone Diels–Alder cycloaddition for the synthesis of the ABD ring system, and finally a highly efficient biomimetic intramolecular O-acylation for the C ring formation. This result provides an important perspective on the biosynthetic origin of the unprecedented 7-membered acyl ketene acetal moiety of the C ring.",

keywords = "Diels–Alder reaction, basiliolide B, biomimetic synthesis, cyclopropanation, O-acylation",

author = "Long Min and Yang Zhang and Xuefeng Liang and Junrong Huang and Wenli Bao and Lee, \{Chi Sing\}",

note = "This work is supported by the National Natural Science Foundation of China (Grant No. 21072008) and the Peking University Shenzhen Graduate School. A special acknowledgement is made to Dr. Wesley Ting-kwok Chan (Hong Kong Polytechnic University) and Prof. Tao Wang (Peking University Shenzhen Graduate School) for the X-ray crystallography of compounds 1 and 8, respectively Publisher Copyright: {\textcopyright} 2014 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2014",

month = oct,

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doi = "10.1002/anie.201405770",

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T1 - A Biomimetic Synthesis of (±)-Basiliolide B

AU - Min, Long

AU - Zhang, Yang

AU - Liang, Xuefeng

AU - Huang, Junrong

AU - Bao, Wenli

AU - Lee, Chi Sing

N1 - This work is supported by the National Natural Science Foundation of China (Grant No. 21072008) and the Peking University Shenzhen Graduate School. A special acknowledgement is made to Dr. Wesley Ting-kwok Chan (Hong Kong Polytechnic University) and Prof. Tao Wang (Peking University Shenzhen Graduate School) for the X-ray crystallography of compounds 1 and 8, respectively Publisher Copyright: © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2014/10/13

Y1 - 2014/10/13

N2 - A highly diastereoselective and practical biomimetic total synthesis of (±)-basiliolide B has been achieved through the study of the two proposed biosynthetic pathways (O-methylation and O-acylation) for the unprecedented 7-methoxy-4,5-dihydro-3H-oxepin-2-one (C ring). The synthesis featured a cyclopropanation/ring opening strategy for establishing the stereogenic centers at C8 and C9, a biomimetic 2-pyrone Diels–Alder cycloaddition for the synthesis of the ABD ring system, and finally a highly efficient biomimetic intramolecular O-acylation for the C ring formation. This result provides an important perspective on the biosynthetic origin of the unprecedented 7-membered acyl ketene acetal moiety of the C ring.

AB - A highly diastereoselective and practical biomimetic total synthesis of (±)-basiliolide B has been achieved through the study of the two proposed biosynthetic pathways (O-methylation and O-acylation) for the unprecedented 7-methoxy-4,5-dihydro-3H-oxepin-2-one (C ring). The synthesis featured a cyclopropanation/ring opening strategy for establishing the stereogenic centers at C8 and C9, a biomimetic 2-pyrone Diels–Alder cycloaddition for the synthesis of the ABD ring system, and finally a highly efficient biomimetic intramolecular O-acylation for the C ring formation. This result provides an important perspective on the biosynthetic origin of the unprecedented 7-membered acyl ketene acetal moiety of the C ring.

KW - Diels–Alder reaction

KW - basiliolide B

KW - biomimetic synthesis

KW - cyclopropanation

KW - O-acylation

U2 - 10.1002/anie.201405770

DO - 10.1002/anie.201405770

M3 - Journal article

SN - 1433-7851

VL - 53

SP - 11294

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JO - Angewandte Chemie. International Edition

JF - Angewandte Chemie. International Edition

IS - 42

ER -

A Biomimetic Synthesis of (±)-Basiliolide B

Abstract

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