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Stereoselective Synthesis of a cis ‐1,2‐Dialkylcyclopentane Building Block and Its Application in Isoprostane Synthesis (5‐ ent ‐F 2c ‐IsoP)
Author(s) -
Elsner Petteri,
Jetter Peter,
Brödner Kerstin,
Helmchen Günter
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800010
Subject(s) - chemistry , wittig reaction , stereoselectivity , diastereomer , cyclopentane , stereochemistry , isoprostanes , aldehyde , yield (engineering) , derivative (finance) , alkyl , total synthesis , lactone , organic chemistry , catalysis , materials science , arachidonic acid , economics , financial economics , metallurgy , enzyme
The all‐ cis substituted cyclopentane 3a , an analogue of the Corey lactone, has been prepared from a readily available nortricyclanone derivative by a five‐step sequence in an overall yield of 34 %. This chiral building block has been applied in total syntheses of two diastereomeric isoprostanes belonging to the 5‐F 2 family: ent ‐5‐F 2c ‐IsoP ( ent ‐ 1 ) and 5‐ epi ‐ ent ‐5‐F 2c ‐IsoP ( ent ‐ 2 ). Key features of the syntheses are the introduction of the two unsaturated alkyl side chains through an E ‐selective Horner–Wadsworth–Emmons reaction with the base‐sensitive syn ‐aldehyde 10 , along with a Z ‐selective Wittig olefination.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)