Asymmetric synthesis of (–)-leiocarpin A via (–)-(S)-goniothalamin employing Julia–Kocienski olefination. Issue 2 (17th January 2016)

• Record Type: Journal Article
• Authors: Meruva, Suresh Babu; Rao K., Raghavendra; Mohammed, Aaseef; Dahanukar, Vilas H.; Kumar, U. K. Syam; Dubey, P. K.
• Is Part Of: Synthetic communications. Volume 46:Issue 2(2016)
• Page Start: 187
• Page End: 196
• Publication Date: 2016-01-17
• Subjects: Acetonide deprotection -- Julia–Kocienski olefination -- lactonization -- Michael addition -- saturated and unsaturated pyranone -- sharpless asymmetric dihydroxylation; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2015.1128546
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: A concise and enantioselective syntheses of antileukemic natural products such as (–)-(S)-goniothalamin and (–)-leiocarpin A has been accomplished in excellent yields. By employing reported conditions on suitable substrates via Julia–Kocienski olefination, intramolecular lactonization, and subsequently dehydroxylative olefination, (–)-(S)-goniothalamin was synthesized. Then Sharpless asymmetric dihydroxylation–intramolecular Michael addition on (–)-(S)-goniothalamin provided (–)-leiocarpin A. GRAPHICAL ABSTRACT: