Total Synthesis of (+)-epi-Condyfoline

• Published in: Organic letters Vol. 21; no. 23; pp. 9594 - 9597
• Main Authors: Kokkonda, Praveen, Andrade, Rodrigo B
• Format: Journal Article
• Language: English
• 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

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...