A Synthesis of (+)‐Oblongolide

Tony Kung Ming Shing, Jun Yang

Research output: Contribution to journalArticle

Abstract

The absolute configuration of natural oblongolide is reassigned as (3aS,5aR,7S,9aS,9bS)‐3a,5a,6,7,8,9,9a,9b‐octahydro‐7,9b‐dimethylnaphtho[1,2‐c]furan‐1(3H)‐one 2 by a 7‐stage synthesis of its enantiomer 1 from (+)‐citronellol involving a regioselective reduction and an intramolecular Diels‐Alder reaction (IMDA) as the key steps. (+)‐Citronellol was converted into methyl (2E,4E,10E)‐(S)‐(+)‐11‐tert‐butoxycarbonyl‐7‐methyl‐undeca‐2,4,10‐trienoate 7 by sequential Lemieux‐Johnson oxidation, Wittig reaction, pyridinium chlorochromate oxidation, and Wadsworth‐Emmons‐Homer alkenation. A regioselective reduction of the methoxycarbonyl group in 7 afforded tert‐butyl (2.E,8E,10E)‐(S)‐(+)‐2,6‐dimethyl‐12‐hydroxy‐dodeca‐2,8,10‐trienoate 8 from which (+)‐oblongolide was readily obtained via an IMDA reaction.

Original languageEnglish
Pages (from-to)709-712
Number of pages4
JournalJournal of the Chinese Chemical Society
Volume42
Issue number4
DOIs
Publication statusPublished - 1995 Jan 1
Externally publishedYes

Fingerprint

Oxidation
Enantiomers
citronellol
pyridinium chlorochromate

Keywords

  • Absolute configuration
  • Citronellol
  • Intramolecular Diels‐Alder reaction
  • Oblongolide

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

A Synthesis of (+)‐Oblongolide. / Shing, Tony Kung Ming; Yang, Jun.

In: Journal of the Chinese Chemical Society, Vol. 42, No. 4, 01.01.1995, p. 709-712.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Yang, Jun. / A Synthesis of (+)‐Oblongolide. In: Journal of the Chinese Chemical Society. 1995 ; Vol. 42, No. 4. pp. 709-712.
@article{408ff8f99db34db1b33d75f1f913d5c7,
title = "A Synthesis of (+)‐Oblongolide",
abstract = "The absolute configuration of natural oblongolide is reassigned as (3aS,5aR,7S,9aS,9bS)‐3a,5a,6,7,8,9,9a,9b‐octahydro‐7,9b‐dimethylnaphtho[1,2‐c]furan‐1(3H)‐one 2 by a 7‐stage synthesis of its enantiomer 1 from (+)‐citronellol involving a regioselective reduction and an intramolecular Diels‐Alder reaction (IMDA) as the key steps. (+)‐Citronellol was converted into methyl (2E,4E,10E)‐(S)‐(+)‐11‐tert‐butoxycarbonyl‐7‐methyl‐undeca‐2,4,10‐trienoate 7 by sequential Lemieux‐Johnson oxidation, Wittig reaction, pyridinium chlorochromate oxidation, and Wadsworth‐Emmons‐Homer alkenation. A regioselective reduction of the methoxycarbonyl group in 7 afforded tert‐butyl (2.E,8E,10E)‐(S)‐(+)‐2,6‐dimethyl‐12‐hydroxy‐dodeca‐2,8,10‐trienoate 8 from which (+)‐oblongolide was readily obtained via an IMDA reaction.",
keywords = "Absolute configuration, Citronellol, Intramolecular Diels‐Alder reaction, Oblongolide",
author = "Shing, {Tony Kung Ming} and Jun Yang",
year = "1995",
month = "1",
day = "1",
doi = "10.1002/jccs.199500095",
language = "English",
volume = "42",
pages = "709--712",
journal = "Journal of the Chinese Chemical Society",
issn = "0009-4536",
publisher = "Chinese Chemical Society",
number = "4",

}

TY - JOUR

T1 - A Synthesis of (+)‐Oblongolide

AU - Shing, Tony Kung Ming

AU - Yang, Jun

PY - 1995/1/1

Y1 - 1995/1/1

N2 - The absolute configuration of natural oblongolide is reassigned as (3aS,5aR,7S,9aS,9bS)‐3a,5a,6,7,8,9,9a,9b‐octahydro‐7,9b‐dimethylnaphtho[1,2‐c]furan‐1(3H)‐one 2 by a 7‐stage synthesis of its enantiomer 1 from (+)‐citronellol involving a regioselective reduction and an intramolecular Diels‐Alder reaction (IMDA) as the key steps. (+)‐Citronellol was converted into methyl (2E,4E,10E)‐(S)‐(+)‐11‐tert‐butoxycarbonyl‐7‐methyl‐undeca‐2,4,10‐trienoate 7 by sequential Lemieux‐Johnson oxidation, Wittig reaction, pyridinium chlorochromate oxidation, and Wadsworth‐Emmons‐Homer alkenation. A regioselective reduction of the methoxycarbonyl group in 7 afforded tert‐butyl (2.E,8E,10E)‐(S)‐(+)‐2,6‐dimethyl‐12‐hydroxy‐dodeca‐2,8,10‐trienoate 8 from which (+)‐oblongolide was readily obtained via an IMDA reaction.

AB - The absolute configuration of natural oblongolide is reassigned as (3aS,5aR,7S,9aS,9bS)‐3a,5a,6,7,8,9,9a,9b‐octahydro‐7,9b‐dimethylnaphtho[1,2‐c]furan‐1(3H)‐one 2 by a 7‐stage synthesis of its enantiomer 1 from (+)‐citronellol involving a regioselective reduction and an intramolecular Diels‐Alder reaction (IMDA) as the key steps. (+)‐Citronellol was converted into methyl (2E,4E,10E)‐(S)‐(+)‐11‐tert‐butoxycarbonyl‐7‐methyl‐undeca‐2,4,10‐trienoate 7 by sequential Lemieux‐Johnson oxidation, Wittig reaction, pyridinium chlorochromate oxidation, and Wadsworth‐Emmons‐Homer alkenation. A regioselective reduction of the methoxycarbonyl group in 7 afforded tert‐butyl (2.E,8E,10E)‐(S)‐(+)‐2,6‐dimethyl‐12‐hydroxy‐dodeca‐2,8,10‐trienoate 8 from which (+)‐oblongolide was readily obtained via an IMDA reaction.

KW - Absolute configuration

KW - Citronellol

KW - Intramolecular Diels‐Alder reaction

KW - Oblongolide

UR - http://www.scopus.com/inward/record.url?scp=84986492537&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84986492537&partnerID=8YFLogxK

U2 - 10.1002/jccs.199500095

DO - 10.1002/jccs.199500095

M3 - Article

VL - 42

SP - 709

EP - 712

JO - Journal of the Chinese Chemical Society

JF - Journal of the Chinese Chemical Society

SN - 0009-4536

IS - 4

ER -