Total synthesis of cladocorans A and B: a structural revision.
Cladocorans A and B, isolated from the Mediterranean coral Cladocora cespitosa, are novel sesterterpenoids whose structures were initially proposed as 1 and 2, respectively. These designations, however, subsequently came under doubt. In the present study, the synthesis of compounds 5 and 6 was undertaken. The physical properties of 5 and 6 were found to be identical to those of natural cladocorans A and B, whose structures were thus concluded to be 5 and 6, respectively. Cladocoran B is thus clearly shown to be an olefinic regioisomer of dysidiolide and cladocoran A as its acetate.
Miyaoka
Hiroaki
H
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Yamanishi
Makoto
M
Kajiwara
Yasuhiro
Y
Yamada
Yasuji
Y
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D007202:Indicators and Reagents; D008522:Mediterranean Sea; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D007202:Indicators and Reagents; C479318:cladocoran A; C121906:dysidiolide; D015107:4-Butyrolactone