Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide.
Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide has been achieved from a single intermediate 26, which was synthesized in 11 steps from a d-mannitol-derived intermediate 8 in an overall yield of 10%. The key steps in the synthesis are inversion of a chiral center by taking an advantage of the inherent mechanism involved in the ring closing to an epoxide via intramolecular S(N)2 reaction and lactonization of a diol using Fetizons reagent. The strategy is amenable to preparation of analogues of (+)-boronolide in sufficient amount for further screening of biological activity.
Chandrasekhar
M
M
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.
Chandra
Kusum L
KL
Singh
Vinod K
VK
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007202:Indicators and Reagents; D007783:Lactones / Q000032:analysis / Q000138:chemical synthesis*; D019686:Lamiaceae / Q000737:chemistry; D008353:Mannitol / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D007202:Indicators and Reagents; D007783:Lactones; C469612:boronolide; C479618:deacetylboronolide; C479619:dideacetylboronolide; D008353:Mannitol