Synthesis of the Macrolactone Cores of Maltepolides via a Diene-Ene Ring-Closing Metathesis Strategy

Man Ki Sit; Hui Hui Cao; Yan Dong Wu; Tsz Chun Yip; Lars Eric Bendel; Wen Zhang; Wei Min Dai

doi:10.1021/acs.orglett.3c00106

Synthesis of the Macrolactone Cores of Maltepolides via a Diene-Ene Ring-Closing Metathesis Strategy

Man Ki Sit, Hui Hui Cao, Yan Dong Wu, Tsz Chun Yip, Lars Eric Bendel, Wen Zhang, Wei Min Dai^*

^*Corresponding author for this work

Department of Chemistry

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

4 Citations (Scopus)

Abstract

Synthesis of the C19-truncated maltepolide E has been accomplished via a diene-ene ring-closing metathesis (RCM) strategy without damage to the C11-C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring opening to furnish the C19-truncated maltepolides A and B as proposed for the biosynthesis of maltepolides.

Original language	English
Pages (from-to)	1633-1637
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.3c00106
Publication status	Published - 17 Mar 2023

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

Access to Document

10.1021/acs.orglett.3c00106

Cite this

@article{93cca3245c094b8d824e4e69cddee7de,

title = "Synthesis of the Macrolactone Cores of Maltepolides via a Diene-Ene Ring-Closing Metathesis Strategy",

abstract = "Synthesis of the C19-truncated maltepolide E has been accomplished via a diene-ene ring-closing metathesis (RCM) strategy without damage to the C11-C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring opening to furnish the C19-truncated maltepolides A and B as proposed for the biosynthesis of maltepolides.",

author = "Sit, \{Man Ki\} and Cao, \{Hui Hui\} and Wu, \{Yan Dong\} and Yip, \{Tsz Chun\} and Bendel, \{Lars Eric\} and Wen Zhang and Dai, \{Wei Min\}",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = mar,

day = "17",

doi = "10.1021/acs.orglett.3c00106",

language = "English",

volume = "25",

pages = "1633--1637",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Synthesis of the Macrolactone Cores of Maltepolides via a Diene-Ene Ring-Closing Metathesis Strategy

AU - Sit, Man Ki

AU - Cao, Hui Hui

AU - Wu, Yan Dong

AU - Yip, Tsz Chun

AU - Bendel, Lars Eric

AU - Zhang, Wen

AU - Dai, Wei Min

PY - 2023/3/17

Y1 - 2023/3/17

N2 - Synthesis of the C19-truncated maltepolide E has been accomplished via a diene-ene ring-closing metathesis (RCM) strategy without damage to the C11-C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring opening to furnish the C19-truncated maltepolides A and B as proposed for the biosynthesis of maltepolides.

AB - Synthesis of the C19-truncated maltepolide E has been accomplished via a diene-ene ring-closing metathesis (RCM) strategy without damage to the C11-C14 alkenyl epoxy unit. Upon release of the C17-OH group, it attacked at the C14 position with double bond migration and epoxide ring opening to furnish the C19-truncated maltepolides A and B as proposed for the biosynthesis of maltepolides.

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000936881600001

UR - https://openalex.org/W4321612040

U2 - 10.1021/acs.orglett.3c00106

DO - 10.1021/acs.orglett.3c00106

M3 - Journal Article

SN - 1523-7060

VL - 25

SP - 1633

EP - 1637

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Synthesis of the Macrolactone Cores of Maltepolides via a Diene-Ene Ring-Closing Metathesis Strategy

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Cite this