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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Bibliographic Details
Published inOrganic letters Vol. 21; no. 23; pp. 9594 - 9597
Main Authors Kokkonda, Praveen, Andrade, Rodrigo B
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.12.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
ASPIDOSPERMATAN
INDOLE ALKALOIDS
DIMETHYL(METHYLTHIO)SULFONIUM FLUOROBORATE
CYCLIZATION
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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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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03762