Asymmetric Total Synthesis of Rollicosin

• Published in: Organic letters Vol. 7; no. 7; pp. 1243 - 1245
• Main Authors: Quinn, Kevin J, Isaacs, André K, DeChristopher, Brian A, Szklarz, Stephanie C, Arvary, Rebecca A
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 31.03.2005; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Combinatorial Chemistry Techniques; Furans - chemical synthesis; Lactones - chemistry; Molecular Structure; Physical Sciences; Plants, Medicinal - chemistry; Rollinia - chemistry; Science & Technology; Stereoisomerism; ANNONACEOUS ACETOGENINS; METATHESIS

The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal γ-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incor...