Formal Total Synthesis of (-)-Raphidecursinol B

• Published in: European Journal of Organic Chemistry Vol. 2010; no. 26; pp. 5100 - 5107
• Main Authors: Kumar Das, Sanjit, Kumar Das, Sajal, Panda, Gautam
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2010; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Antibiotics; Chemistry; Chemistry, Organic; Epoxides; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Natural products; Noncondensed benzenic compounds; Organic chemistry; Oxyneolignan; Physical Sciences; Preparations and properties; Science & Technology; Total synthesis; ABSOLUTE-CONFIGURATION ASSIGNMENT; IN-VITRO; Antibiotics; ENANTIOSELECTIVE SYNTHESIS; Natural products; Oxyneolignan; STEREOSELECTIVE-SYNTHESIS; Epoxides; NEOLIGNANS; Total synthesis; VIROLA; Antimalarial; Stereoisomer; Enantioselectivity; Regioselectivity; Mitsunobu reaction; Natural compound; Oxygen heterocycle; Ring cleavage; Antibiotic; Asymmetric synthesis; Sharpless dihydroxylation; Epoxide; Benzenic compound; Tosylation; Benzaldehyde derivatives
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201000619

An efficient enantioselective formal total synthesis of antimalarial natural product (–)‐raphidecursinol B along with its all stereoisomers is described from commercially available 3,4,5‐trimethoxybenzaldehyde using the Sharpless asymmetric dihydroxylation, regioselective α‐tosylation, epoxide opening and Mitsunobu reaction as the key reaction steps. An efficient enantioselective formal total synthesis of the antimalarial natural product (–)‐raphidecursinol B along with its all stereoisomers is described, starting from commercially available 3,4,5‐trimethoxybenzaldehyde.