Stereoselective synthesis of naturally occurring α-methylenebis-γ-butyrolactones: An application of novel oxiranyl "remote" anions

J. Lertvorachon; Y. Thebtaranonth; T. Thongpanchang; P. Thongyoo

doi:10.1021/jo010259f

Stereoselective synthesis of naturally occurring α-methylenebis-γ-butyrolactones: An application of novel oxiranyl "remote" anions

J. Lertvorachon
, Y. Thebtaranonth
, T. Thongpanchang
, P. Thongyoo

Mahidol University

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

37 Citations (Scopus)

Abstract

Stereospecific deprotonation of the epoxy proton at the β-position of the α,β-epoxy esters 5 and 6 yielded oxiranyl "remote" anions 7 and 8, which could then be used for alkylation. The anions 7 and 8 underwent a consecutive aldol lactonization to give, respectively, epoxy lactones 11 and 13 with high stereoselectivity. Generation of the remote anions as well as their stereoselective reactions served as a new synthetic route to the naturally occurring α-methylenebis-γ-butyrolactones, 1.

Original language	English
Pages (from-to)	4692-4694
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	66
Issue number	13
DOIs	https://doi.org/10.1021/jo010259f
Publication status	Published - 29 Jun 2001
Externally published	Yes

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title = "Stereoselective synthesis of naturally occurring α-methylenebis-γ-butyrolactones: An application of novel oxiranyl {"}remote{"} anions",

abstract = "Stereospecific deprotonation of the epoxy proton at the β-position of the α,β-epoxy esters 5 and 6 yielded oxiranyl {"}remote{"} anions 7 and 8, which could then be used for alkylation. The anions 7 and 8 underwent a consecutive aldol lactonization to give, respectively, epoxy lactones 11 and 13 with high stereoselectivity. Generation of the remote anions as well as their stereoselective reactions served as a new synthetic route to the naturally occurring α-methylenebis-γ-butyrolactones, 1.",

author = "J. Lertvorachon and Y. Thebtaranonth and T. Thongpanchang and P. Thongyoo",

year = "2001",

month = jun,

day = "29",

doi = "10.1021/jo010259f",

language = "English",

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journal = "Journal of Organic Chemistry",

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T1 - Stereoselective synthesis of naturally occurring α-methylenebis-γ-butyrolactones

T2 - An application of novel oxiranyl "remote" anions

AU - Lertvorachon, J.

AU - Thebtaranonth, Y.

AU - Thongpanchang, T.

AU - Thongyoo, P.

PY - 2001/6/29

Y1 - 2001/6/29

N2 - Stereospecific deprotonation of the epoxy proton at the β-position of the α,β-epoxy esters 5 and 6 yielded oxiranyl "remote" anions 7 and 8, which could then be used for alkylation. The anions 7 and 8 underwent a consecutive aldol lactonization to give, respectively, epoxy lactones 11 and 13 with high stereoselectivity. Generation of the remote anions as well as their stereoselective reactions served as a new synthetic route to the naturally occurring α-methylenebis-γ-butyrolactones, 1.

AB - Stereospecific deprotonation of the epoxy proton at the β-position of the α,β-epoxy esters 5 and 6 yielded oxiranyl "remote" anions 7 and 8, which could then be used for alkylation. The anions 7 and 8 underwent a consecutive aldol lactonization to give, respectively, epoxy lactones 11 and 13 with high stereoselectivity. Generation of the remote anions as well as their stereoselective reactions served as a new synthetic route to the naturally occurring α-methylenebis-γ-butyrolactones, 1.

UR - https://www.scopus.com/pages/publications/0035967750

U2 - 10.1021/jo010259f

DO - 10.1021/jo010259f

M3 - Article

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AN - SCOPUS:0035967750

SN - 0022-3263

VL - 66

SP - 4692

EP - 4694

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Stereoselective synthesis of naturally occurring α-methylenebis-γ-butyrolactones: An application of novel oxiranyl "remote" anions

Abstract

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