- Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: Exploiting combinatorial catalysis
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A streamlined entry into the sesquiterpene lactone (SQL) cores of linearifolin and zaluzanin A is described. Stereochemistry is controlled through transformations uncovered by ISES (In Situ Enzymatic Screening). Absolute stereochemistry derives from kinet
- Ginotra, Sandeep K.,Friest, Jacob A.,Berkowitz, David B.
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- Total synthesis of a nonclassical bioactive acetogenin, (+)-muconin
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A convergent total synthesis of the tetrahydropyran-bearing acetogenin (+)-muconin 1 is described. All five chiral building blocks 7, 9, 17, 21, and 29 were prepared from D-glutamic acid, respectively. Four out of them were used to furnish the alkyne 16 and the iodoalkyne 33, respectively, and palladium(0)-mediated cross-coupling of alkynes 16 and 33, followed by hydrogenation, afforded 36. Simultaneous deprotection of the MOM and TBS groups in 36 with BF3·Et2O in the presence of Me2S provided (+)-muconin 1. (C) 2000 Elsevier Science Ltd.
- Yang, Wen-Qian,Kitahara, Takeshi
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p. 1451 - 1461
(2007/10/03)
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