Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones | Zendy

José Manuel BotubolAres | Zendy; María Jesús DuránPeña | Zendy; Antonio J. MacíasSánchez | Zendy; James R. Hanson | Zendy; Isidro G. Collado | Zendy; Rosario HernándezGalán | Zendy

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Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones

Author(s) -

José Manuel BotubolAres,

María Jesús DuránPeña,

Antonio J. MacíasSánchez,

James R. Hanson,

Isidro G. Collado,

Rosario HernándezGalán

Publication year - 2014

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/c4ob00717d

Subject(s) - chemistry , polyketide , diversity (politics) , stereochemistry , combinatorial chemistry , organic chemistry , biosynthesis , enzyme , sociology , anthropology

The enantioselective synthesis of (2R,3R,4E,8E)-3-hydroxy-2,4,8-trimethyldeca-4,8-dienolide (5) by ring-closing metathesis is described. This compound is an analogue of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (4) which is a rare 11-membered lactone produced by the fungus, Botrytis cinerea. Mutasynthetic studies with compound 5 using two mutants of B. cinerea led to the isolation of four new highly oxygenated 11-membered lactones (11-14) in which compound 5 has been stereoselectively epoxidized and hydroxylated at sites that were not easily accessible by classical synthetic chemistry.

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