Synthesis of the northern fragment of an epothilone D analogue from (−)-carvone

Muscarine, imidazole, oxazole and thiazole alkaloids

“…247,250 In addition, a northern ring-opening fragment was also prepared from (À)-carvone during the synthesis of epothilone D analogues. 251 As a type of natural polyketide, the thuggacins A-C 371-373 rst isolated from myxobacterium Sorangium cellulosum have received extensive interest due to their strong anti-bacterial activity. Thirteen new analogues of the natural thuggacins A-C were recently synthesized by total and semi-synthesis methods.…”

Diastereoselective Synthesis of 7,8-Carvone Epoxides

“…Due to the importance of the natural epoxides 3 and 4 for the synthesis of natural products [35], where they act as starting materials, there has been a great interest in their synthesis. Notwithstanding this, to the best of our knowledge, they have not been separated or obtained separately.…”

Alternative synthesis of thiazole-substituted fragment C10-C21 of epothilone D analog

“…In our previously published synthesis of compound 2 [4] methyl ketone 3 obtained from R-(-)-carvone was olefinated with ylide generated in situ from phosphonium salt 4 in the final stages of the synthesis. In the course of optimization of compound 2 synthesis we found that highly reactive diketone 5 easily prepared from R-(-)carvone reacted with ylide generated from salt 4 exclusively regioselectively.…”

“…Wittig reaction proceeded fast even at -78°С affording compound 6 in 95% yield. The reaction time shortened to one hour, whereas the coupling of the thiazole block 4 with ketone 3 proceeded within 12 h [4]. New synthon 6 underlies the more effective synthesis of compound 2 (Scheme 2).…”