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Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.

ABSTRACT: Under the conditions of C-C bond forming transfer hydrogenation, 1,3-propanediol 1 engages in double asymmetric carbonyl allylation to furnish the C(2)-symmetric diol 2. Double ozonolysis of 2 followed by TBS protection delivers aldehyde 3, which is subject to catalyst directed carbonyl reverse prenylation via transfer hydrogenation to deliver neopentyl alcohol 4 and, ultimately, the bryostatin A-ring 7. Through use of two consecutive C-C bond forming transfer hydrogenations, the Evans' bryostatin A-ring 7 is prepared in less than half the manipulations previously reported.

SUBMITTER: Lu Y

PROVIDER: S-EPMC2727624 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

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Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.

Lu Yu Y Krische Michael J MJ

Organic letters 20090701 14

Under the conditions of C-C bond forming transfer hydrogenation, 1,3-propanediol 1 engages in double asymmetric carbonyl allylation to furnish the C(2)-symmetric diol 2. Double ozonolysis of 2 followed by TBS protection delivers aldehyde 3, which is subject to catalyst directed carbonyl reverse prenylation via transfer hydrogenation to deliver neopentyl alcohol 4 and, ultimately, the bryostatin A-ring 7. Through use of two consecutive C-C bond forming transfer hydrogenations, the Evans' bryostat ...[more]

PMID: 19586066

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