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Convergent and Efficient Total Synthesis of (+)-Heilonine Enabled by C-H Functionalizations.

ABSTRACT: We report a convergent and efficient total synthesis of the C-nor D-homo steroidal alkaloid (+)-heilonine with a hexacyclic ring system, nine stereocenters, and a trans-hydrindane moiety. Our synthesis features four selective C-H functionalizations to form key C-C bonds and stereocenters, a Stille carbonylative cross-coupling to connect the AB ring system with the DEF ring system, and a Nazarov cyclization to construct the five-membered C ring. These enabling transformations significantly reduced functional group manipulations and delivered (+)-heilonine in 11 or 13 longest linear sequence (LLS) steps.

SUBMITTER: Jin Y

PROVIDER: S-EPMC10811669 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Convergent and Efficient Total Synthesis of (+)-Heilonine Enabled by C-H Functionalizations.

Jin Yuan Y Hok Sovanneary S Bacsa John J Dai Mingji M

Journal of the American Chemical Society 20240116 3

We report a convergent and efficient total synthesis of the C-nor D-homo steroidal alkaloid (+)-heilonine with a hexacyclic ring system, nine stereocenters, and a trans-hydrindane moiety. Our synthesis features four selective C-H functionalizations to form key C-C bonds and stereocenters, a Stille carbonylative cross-coupling to connect the AB ring system with the DEF ring system, and a Nazarov cyclization to construct the five-membered C ring. These enabling transformations ...[more]

PMID: 38226869

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