Synthesis of the C‐8–C‐24 Fragment of Maltepolide C by Using a Tandem Di­hydroxylation/SN2 Cyclization Sequence. Issue 23 (2nd July 2015)

• Record Type: Journal Article
• Authors: Mohapatra, Debendra K.; Reddy, D. Sai; Reddy, G. Sudhakar; Yadav, Jhillu S.
• Is Part Of: European journal of organic chemistry. Issue 23(2015)
• Page Start: 5266
• Page End: 5274
• Publication Date: 2015-07-02
• Subjects: Asymmetric synthesis -- Natural products -- Dihydroxylation -- Cyclization -- Lactones -- Macrocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500629
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A highly stereoselective synthesis of the C‐8–C‐24 fragment of maltepolide C has been achieved in a convergent and efficient manner by utilizing a tandem Sharpless asymmetric dihydroxylation (SAD)/SN 2 cyclization reaction sequence as the key step. Other important steps include a Crimmins‐modified Evans aldol reaction, a Brown asymmetric allylation, a Horner–Wadsworth–Emmons olefination, and a Corey–Bakshi–Shibata (CBS) reduction. Abstract : A highly stereoselective synthesis of the C‐8–C‐24 fragment of maltepolide C has been achieved in a convergent and efficient manner by utilizing a tandem Sharpless asymmetric dihydroxylation (SAD)/SN 2 cyclization reaction sequence as the key step.