Total Synthesis of (+)-epi-Condyfoline
Herein, we report the first asymmetric total synthesis of aspidospermatan indole alkaloid (+)-epi-condyfoline (1) in 15 steps from commercially available 2-methylindole-3-carboxaldehyde. Key steps include (1) our domino Michael/Mannich annulation method of N-sulfinyl metallodienamines to set three c...
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Published in | Organic letters Vol. 21; no. 23; pp. 9594 - 9597 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
06.12.2019
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | Herein, we report the first asymmetric total synthesis of aspidospermatan indole alkaloid (+)-epi-condyfoline (1) in 15 steps from commercially available 2-methylindole-3-carboxaldehyde. Key steps include (1) our domino Michael/Mannich annulation method of N-sulfinyl metallodienamines to set three contiguous stereocenters, (2) LiHMDS-mediated cyclization of an ω-tosyloxy N-sulfinamide to prepare the signature indole-fused 2-azabicyclo[3.3.1]nonane framework, and (3) DMTSF-promoted spirocyclization of a dithioacetal intermediate to access the final pyrrolidine ring. Functional group manipulations delivered the targeted alkaloid (+)-epi-condyfoline (1) in 13 steps and 1.25% overall yield from N-sulfinylimine (+)-8. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.9b03762 |