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

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

研究成果: Article査読

28 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)8595-8607
ページ数13
ジャーナルJournal of Organic Chemistry
65
25
DOI
出版ステータスPublished - 2000 12月 15

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル