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Kokkonda P , Andrade RB
Total Synthesis of (+)-epi-Condyfoline
Org Lett. 2019 Dec 6;21(23) :9594-9597
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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 omega-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.
1523-7052 Kokkonda, Praveen Andrade, Rodrigo B ORCID: http://orcid.org/0000-0002-4554-8323 Journal Article United States Org Lett. 2019 Nov 18. doi: 10.1021/acs.orglett.9b03762.