Total Synthesis of Gossypol

Indoleacetic Acid Oxidizing Enzyme & Inhibitors from Light-Grown Cotton

“…Gossvpol, a phenolic substance found( in cotton seed, leaves, ain(l roots ( 21 ), has certain struictural sinmilarities (5 ) to an IAA oxidlase inhibitor in peas (19). Gossvpol acted as a potent inhibitor of the cotton leaf enzyme (table I' idenitifiedI in peas (6,19), functionedl in our assay system in a miianlner idlentical to gossvpol and the lnatuiral inhibitor fromii cotton (fig 5 & 7).…”

Reaction chemistry of gossypol and its derivatives

“…Of paramount importance to this endeavor is the synthesis of apogossypol (19, Fig. 12) in 5% overall yield by Edwards and Cashaw (36)(37)(38). From this pioneering work, much research (47,54,56,175,(184)(185)(186)(187)(188)(189)(190)(191)(192)(193) has followed to devise new, higher-yielding methodologies to prepare gossypol's basic naphthalene framework.…”

“…Almost two decades passed after Adams' initial studies before the structure postulated by Adams for gossypol was confirmed through gossypol's total synthesis, completed by Edwards and colleague (36)(37)(38). With gossypol's structure now firmly established, researchers turned to improving cottonseed's meal and oil quality by developing methods to remove gossypol and other gossypol-like pigments.…”

Synthesis of hemigossypol and its derivatives

“…Vilsmeier and N,N-diphenylformamidine methods did not afford product. 36, 37, 38 The Duff reaction, which involves the use of hexamethylenetetramine in the presence of acetic acid, on compound 9b gave the dehydrated compound 10b in a 25% yield. 39 These disappointing results led to the one pot reaction of compound 7a with boron tribromide followed by triethylorthoformate to give compound 11 in 25% yield.…”