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Enantioselective Synthesis of the Ethyl Analog of the Marine Alkaloid Haliclorensin C.

ABSTRACT: The enantioselective synthesis (3.7% overall yield in nine steps from 2) and biological screening of the ethyl analog of the macrocyclic marine alkaloid haliclorensin C (compound 5) are reported. Amino alcohol 3, generated by a LiNH?BH?-promoted reductive ring-opening/debenzylation sequence from phenylglycinol-derived lactam 2, was used as the starting chiral linear building block. Incorporation of the undecene chain via the nosyl derivative 12, methylenation of the pentanol moiety, and a ring-closing metathesis are the key steps of the synthesis.

SUBMITTER: Guignard G

PROVIDER: S-EPMC6470606 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of the Ethyl Analog of the Marine Alkaloid Haliclorensin C.

Guignard Guillaume G Llor Núria N Pubill David D Bosch Joan J Amat Mercedes M

Molecules (Basel, Switzerland) 20190318 6

The enantioselective synthesis (3.7% overall yield in nine steps from 2) and biological screening of the ethyl analog of the macrocyclic marine alkaloid haliclorensin C (compound 5) are reported. Amino alcohol 3, generated by a LiNH₂BH₃-promoted reductive ring-opening/debenzylation sequence from phenylglycinol-derived lactam 2, was used as the starting chiral linear building block. Incorporation of the undecene chain via the nosyl derivative 12, methylenation o ...[more]

PMID: 30889939

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