Total Synthesis of Phorboxazole B
- 13 January 2006
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 12 (4) , 1185-1204
- https://doi.org/10.1002/chem.200500892
Abstract
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.Keywords
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