01593nas a2200229   4500008004100000022001400041245014600055210006900201260007700270300001400347520068100361653002501042653002501067653002101092653001201113653002401125653002001149100002401169700002401193700002401217856012201241       2014                        eng d  a1434-193X00aProtecting-group-free diastereoselective total synthesis of (+/-)-6-epi-cleistenolide and chemoenzymatic synthesis of (-)-6-epi-cleistenolide0 aProtectinggroupfree diastereoselective total synthesis of 6epicl  aBOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANYbWILEY-V C H VERLAG GMBHcDEC  a8049-80543 a<p>A short, efficient, practical, and protecting-group-free diastereoselective total synthesis of (+/-)-6-epi-cleistenolide (1) has been achieved in five steps in 60% overall yield. The use of a chemoenzymatic approach also gave (-)-6-epi-cleistenolide (1) (&gt;99.9% ee). The Achmatowicz reaction, chemoselective oxidation of a hemiacetal, diastereoselective 1,3-anti reduction of alpha-hydroxy ketone, and enzymatic resolution of a 1,3-diol are the key features of this linear total synthesis. The synthetic strategy demonstrated in this paper could be extended for an asymmetric total synthesis of (-)-cleistenolide (1) and related biologically active natural products.</p>10aAsymmetric synthesis10adiastereoselectivity10aEnzyme catalysis10aLipases10aOxygen heterocycles10aTotal synthesis1 aMahajan, Pankaj, S.1 aGonnade, Rajesh, G.1 aMhaske, Santosh, B.  uhttps://library.ncl.res.in/content/protecting-group-free-diastereoselective-total-synthesis-6-epi-cleistenolide-and-0