Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid

Y. Suzuki, R. Nishimaki, M. Ishikawa, T. Murata, Kenichi Takao, K. I. Tadano

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

We have achieved the total synthesis of (-)-mniopetal E, a drimane sesquiterpenoid which inhibits the reverse transcriptase of human immunodeficiency virus (HIV)-1. Our enantiospecific total synthesis of this target molecule in naturally occurring form commenced with a known 2,3-anhydro-D-arabinitol derivative, which was prepared using the Sharpless asymmetric epoxidation strategy. The key steps of our total synthesis were as follows: (1) a combination of highly stereocontrolled inter- and intramolecular Horner-Emmons carbon elongations for construction of a butenolide tethering a 1,2,4,9-functionalized nona-5,7-diene moiety at the β-carbon, (2) stereoselective thermal intramolecular Diels-Alder reaction of the thus-formed trienic compound, providing preferentially an endo-cycloadduct with the desired π-facial selection, and (3) efficient transformation of the γ-lactone moiety in the major cycloadduct to the γ-hydroxy-γ-lactone part in mniopetal E. Our total synthesis of (-)-mniopetal E established the unsettled absolute stereochemistry of the antibiotic.

Original languageEnglish
Pages (from-to)8595-8607
Number of pages13
JournalJournal of Organic Chemistry
Volume65
Issue number25
DOIs
Publication statusPublished - 2000 Dec 15

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Lactones
Carbon
Stereochemistry
Epoxidation
Elongation
Anti-Bacterial Agents
Derivatives
Molecules
mniopetal E
drimane
Hot Temperature
Human immunodeficiency virus 1 reverse transcriptase
butenolide
arabitol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid. / Suzuki, Y.; Nishimaki, R.; Ishikawa, M.; Murata, T.; Takao, Kenichi; Tadano, K. I.

In: Journal of Organic Chemistry, Vol. 65, No. 25, 15.12.2000, p. 8595-8607.

Research output: Contribution to journalArticle

Suzuki, Y. ; Nishimaki, R. ; Ishikawa, M. ; Murata, T. ; Takao, Kenichi ; Tadano, K. I. / Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid. In: Journal of Organic Chemistry. 2000 ; Vol. 65, No. 25. pp. 8595-8607.
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