Enantiospecific total synthesis of (-)-bakkenolide III and formal total synthesis of (-)-bakkenolides B, C, H, L, V, and X.
A concise enantiospecific synthesis of (-)-bakkenolide III was accomplished from (S)-(+)-carvone. The key step involved radical cyclization of an iodoketone intermediate which afforded the cis-hydrindanone skeleton. Further synthetic transformations generated bakkenolide III, which also constitutes the formal total synthesis of (-)-bakkenolides, B, C, H, L, V, and X.
Jiang
Chiao-Hua
CH
Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan, ROC.
Bhattacharyya
Annyt
A
Sha
Chin-Kang
CK
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D007189:Indans / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D039821:Monoterpenes / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis; D013141:Spiro Compounds / Q000138:chemical synthesis*
D000081005:Cyclohexane Monoterpenes; D007189:Indans; D007659:Ketones; D039821:Monoterpenes; D012717:Sesquiterpenes; D013141:Spiro Compounds; C110814:bakkenolide G; C523378:bakkenolide III; C006923:carvone; D015107:4-Butyrolactone