Total Synthesis and Structure–Activity Relationship Studies of the Cytotoxic Anhydrophytosphingosine Jaspine B (Pachastrissamine)
Received: 09.09.216Received: 09.09.216
Accepted after revision: 16 November 2016
19 December 2016 (eFirst)
Dedicated to Professor Hiriyakkanavar Junjappa on the occasion of his 80th birthday
By utilizing an l-serine-derived bicyclic lactone as an advanced chiral building block, a short synthetic route to the cytotoxic marine natural product jaspine B has been developed. Targeting structure–activity relationship investigations, the synthetic route has also been utilized for the synthesis and cytotoxicity evaluation of strategically modified jaspine B analogues. In addition, a previously reported synthesis of the title natural product from our research has been reinvestigated to clarify the sterochemical assignment.