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Stereoselective Synthesis of the C1-C16 Fragment of the Purported Structure of Formosalide B.

ABSTRACT: The first stereoselective synthesis of the C1-C16 fragment possessing stereo-enriched fully substituted tetrahydropyran (THP) along with tetrahydrofuran (THF) rings of the proposed structure of formosalide B is described in 12 longest linear steps with 22% overall yield, starting from two cheap and commercially available 1,5-pentanediol and l-glutamic acid, following a convergent approach. The key steps involve in this synthesis are Horner-Wadsworth-Emmons reaction, Sharpless asymmetric dihydroxylation, and acid-mediated ketalization to assemble the substituted THP ring, one-pot Sharpless dihydroxylation-SN2-type cyclization, and Wittig homologation to construct the THF derivative.

SUBMITTER: Gajula S

PROVIDER: S-EPMC7203982 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of the C1-C16 Fragment of the Purported Structure of Formosalide B.

Gajula Srinivas S Vishnu V Reddy Aedula A Reddy D Prabhakar DP Yadav Jhillu S JS Mohapatra Debendra K DK

ACS omega 20200423 17

The first stereoselective synthesis of the C1-C16 fragment possessing stereo-enriched fully substituted tetrahydropyran (THP) along with tetrahydrofuran (THF) rings of the proposed structure of formosalide B is described in 12 longest linear steps with 22% overall yield, starting from two cheap and commercially available 1,5-pentanediol and l-glutamic acid, following a convergent approach. The key steps involve in this synthesis are Horner-Wadsworth-Emmons reaction, Sharpless asymmetric dihydrox ...[more]

PMID: 32391510

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