Publication:
General strategy for stereoselective synthesis of 1-substituted Exo,Endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Total synthesis of (±)-gmelinol

Issued Date

2006-01-06

Resource Type

Article

ISSN

00223263

DOI

10.1021/jo0519110

Other identifier(s)

2-s2.0-31144470193

Rights

Mahidol University

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SCOPUS

Bibliographic Citation

Journal of Organic Chemistry. Vol.71, No.1 (2006), 386-389

Suggested Citation

Manat Pohmakotr, Attapol Pinsa, Tipwan Mophuang, Patoomratana Tuchinda, Samran Prabpai, Palangpon Kongsaeree, Vichai Reutrakul General strategy for stereoselective synthesis of 1-substituted Exo,Endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Total synthesis of (±)-gmelinol. Journal of Organic Chemistry. Vol.71, No.1 (2006), 386-389. doi:10.1021/jo0519110 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/23182

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Title

General strategy for stereoselective synthesis of 1-substituted Exo,Endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Total synthesis of (±)-gmelinol

Author(s)

Manat Pohmakotr
 Attapol Pinsa
 Tipwan Mophuang
 Patoomratana Tuchinda
 Samran Prabpai
 Palangpon Kongsaeree
 Vichai Reutrakul

Other Contributor(s)

Mahidol University

Abstract

A general strategy for stereoselective synthesis of 1-substituted exo,endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes including (±)-gmelinol from (2,3-trans)-(4,5-cis)-α-aroylparaconic esters, which are readily obtained from the reaction of vicinal dianions derived from α- aroylsuccinic esters with aromatic aldehydes, is described. The synthetic sequence involves α-methylation or α-hydroxylation, reduction, bislactonization, and reduction followed by furofuran formation. © 2006 American Chemical Society.

Keyword(s)

Chemistry

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/23182

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Scopus 2006-2010