Kim Jin Hyo, Curtis-Long Marcus J, Seo Woo Duck, Ryu Young Bae, Yang Min Suk, Park Ki Hun
Department of Agricultural Chemistry, Division of Applied Life Science (BK21 programs), Gyeongsang National University, Jinju, 660-701, South Korea.
J Org Chem. 2005 May 13;70(10):4082-7. doi: 10.1021/jo050079w.
[structures: see text] Enantiomerically pure 2-alkyl-3-acetoxy-4-iodopyrrolidines with all groups cis, and all adjacent groups trans (10 and 17), important precursors for the synthesis of pyrrolidinediols, have been prepared from D-tyrosine through regio- and diastereoselective reduction of a vinyl ketone and subsequent iodoamidation controlled by minimization of nonbonding steric interactions. Highly stereodivergent Woodward-Prevost methodology, applied to both iodopyrrolidines, yielded enantiomerically pure (2R,3R,4R)-, (2R,3R,4S)-, and (2R,3S,4R)-deacetylanisomycin (3, 4, and 5), each in excellent de. Incorporation of differential protection of the hydroxyl groups led to a one-pot synthesis of (2R,3R,4R)-anisomycin 2.
[结构：见正文] 具有所有基团顺式以及所有相邻基团反式的对映体纯的2-烷基-3-乙酰氧基-4-碘代吡咯烷（10和17）是合成吡咯烷二醇的重要前体，它们是由D-酪氨酸通过乙烯基酮的区域和非对映选择性还原以及随后通过最小化非键合空间相互作用控制的碘代酰胺化反应制备的。应用于两种碘代吡咯烷的高度立体发散性伍德沃德-普雷沃斯特方法，得到了对映体纯的(2R,3R,4R)-、(2R,3R,4S)-和(2R,3S,4R)-脱乙酰基茴香霉素（3、4和5），每种的de值都很高。引入羟基的差异保护导致了(2R,3R,4R)-茴香霉素2的一锅法合成。
