177607-90-8Relevant academic research and scientific papers
Total asymmetric synthesis of the potent immunosuppressive marine natural product microcolin A
Decicco, Carl P.,Grover, Paul
, p. 3534 - 3541 (1996)
The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported. The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.
Highly Convergent Total Synthesis and Assignment of Absolute Configuration of Majusculamide D, a Potent and Selective Cytotoxic Metabolite from Moorea sp.
Caro-Diaz, Eduardo J. E.,Valeriote, Frederick A.,Gerwick, William H.
, p. 793 - 796 (2019/02/07)
The total synthesis of majusculamide D (MJS-D) is described, a lipopentapeptide originally isolated from Lyngbya majuscula and reisolated from a Moorea sp. MJS-D possesses selective and potent cancer cell toxicity. A scalable and convergent strategy with a minimal number of purifications produced significant quantities of MJM-D for in vivo evaluations. The absolute configuration of the 1,3-dimethyl-octanamide motif was determined by synthesis of this fragment via ZACA chemistry.
