Total synthesis of phorboxazole B.
An efficient and highly convergent total synthesis of the potent antitumor agent phorboxazole B has been achieved. The synthetic strategy of this synthesis features: 1) a highly efficient substrate-controlled hydrogenation to construct the functionalized cis-tetrahydropyrane unit; 2) iterative crotyl addition to synthesize the segment that contains alternating hydroxyl and methyl substituents; 3) Hg(OAc)2/I2-induced cyclization to establish the cis-tetrahydropyrane moiety; 4) 1,3-asymmetric induction in the Mukaiyama aldol reaction to afford the stereogenic centers at C9 and C3; and 5) the exploration of the Still-Gennari olefination reaction to complete the macrolide ring of phorboxazoloe B.
Li
De-Run
DR
Shanghai Institute of Organic Chemistry, 354 Fenglin Rd, Shanghai 200032, PR China.
Zhang
Dong-Hui
DH
Sun
Cai-Yun
CY
Zhang
Ji-Wen
JW
Yang
Li
L
Chen
Jian
J
Liu
Bo
B
Su
Ce
C
Zhou
Wei-Shan
WS
Lin
Guo-Qiang
GQ
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*
D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; C408887:phorboxazole A