Canoy Will L, Cooley Bob E, Corona John A, Lovelace Thomas C, Millar Alan, Weber Aimee M, Xie Shiping, Zhang Yong
Chemical Development, GlaxoSmithKline, Research Triangle Park, NC 27709, USA.
Org Lett. 2008 Mar 20;10(6):1103-6. doi: 10.1021/ol703061u. Epub 2008 Feb 22.
A one-step diastereoselective (up to 98:2) synthesis of the bis-furan alcohol of Darunavir and other HIV drug candidates has been achieved utilizing the novel cyclization of glycolaldehyde and 2,3-dihydrofuran. The cycloaddition was catalyzed by a variety of catalysts including those formed from tin(II) triflate and common chiral ligands such as BINAP and Evans's box ligands. An efficient and unique enzymatic process enhanced the enantiomeric purity to provide the target in optically pure form.
利用乙醇醛和2,3 - 二氢呋喃的新型环化反应，实现了达芦那韦双呋喃醇及其他抗HIV候选药物的一步非对映选择性合成（高达98:2）。环加成反应由多种催化剂催化，包括由三氟甲磺酸锡(II)与常见手性配体（如联萘二苯膦和埃文斯盒式配体）形成的催化剂。一种高效且独特的酶促过程提高了对映体纯度，从而以光学纯形式提供目标产物。
