A new strategy for the synthesis of crucigasterin A, and cytotoxic activity of this compound and its related analogues.
Stereoselective total synthesis of bioactive marine natural product crucigasterin A has been accomplished from commercially available and inexpensive L-(-)-malic acid as a starting material. Julia olefination and chelation controlled Grignard additions are the key steps involved in the present synthesis. Cytotoxic properties of crucigasterin A and its related analogues crucigasterins B and D have been evaluated. Crucigasterin A showed promising activities against both the human cervical cancer cell line and human breast adenocarcinoma cell line.
Natural Product Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500607, India.
Jayprakash Narayan
JN
Kumar
Parigi Raghavendar
PR
Reddy
Biswanath
B
Das
C Ganesh
CG
Kumar
Pombala
P
Sujitha
D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D000605:Amino Alcohols; D000970:Antineoplastic Agents; C587419:crucigasterin A
Chelation controlled Grignard addition; Crucigasterin A; Cytotoxicity; Julia olefination; Total synthesis