Synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O. Issue 42 (17th October 2018)

• Record Type: Journal Article
• Authors: Okada, Takuya; Yamamoto, Taiga; Kato, Daiki; Kawasaki, Masashi; Saporito, Ralph A.; Toyooka, Naoki
• Is Part Of: Tetrahedron letters. Volume 59:Issue 42(2018)
• Page Start: 3797
• Page End: 3800
• Publication Date: 2018-10-17
• Subjects: Asymmetric synthesis -- Neotropical poison frog -- Pumiliotoxin -- 8-Deoxypumiliotoxin 193H -- 9-Deoxyhomopumiliotoxin 207O; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.09.015
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The enantiodivergent synthesis of 8-deoxy-PTX193H and 9-deoxy-hPTX207O has been achieved. The enantiopure alcohol (−)-8 was obtained by bakers' yeast reduction of (±)-7 . Enantiomerically pure alcohols (+)- and (−)-10 were obtained by kinetic resolution of racemic10 . The aldol adducts for indolizidinone14 and quinolizidinone21 were opposite. Abstract: The asymmetric synthesis of 8-deoxypumiliotoxin193H and 9-deoxyhomopumiliotoxin207O has been achieved, starting from both enantiomers of (+)- and (−)-10 . Enantiomerically pure alcohols (+)- and (−)-10 were obtained by lipase-mediated kinetic resolution of racemic10, which was prepared in 3 steps from new lactam-type building block (−)-8 in a highly stereoselective manner.