Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton

Kenichi Takao, Hiroyuki Yasui, Shun Yamamoto, Daisuke Sasaki, Soujiro Kawasaki, Gohshi Watanabe, Kin Ichi Tadano

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

The total syntheses of (+)-mycoepoxydiene and (-)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing for the concise construction of the 9-oxabicyclo-[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2- ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (-)-1893A was also synthesized via the vinylogous aldol reaction.

Original languageEnglish
Pages (from-to)8789-8795
Number of pages7
JournalJournal of Organic Chemistry
Volume69
Issue number25
DOIs
Publication statusPublished - 2004 Dec 10

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Biological Products
Stereochemistry
ROM
Derivatives
mycoepoxydiene
furfuryl alcohol
1,3-butadiene
3-hydroxybutanal

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A : Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton. / Takao, Kenichi; Yasui, Hiroyuki; Yamamoto, Shun; Sasaki, Daisuke; Kawasaki, Soujiro; Watanabe, Gohshi; Tadano, Kin Ichi.

In: Journal of Organic Chemistry, Vol. 69, No. 25, 10.12.2004, p. 8789-8795.

Research output: Contribution to journalArticle

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