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Asymmetric Synthesis of ES‐285, an Anticancer Agent Isolated from Marine Sources
Author(s) -
Allepuz Ana C.,
Badorrey Ramón,
DíazdeVillegas María D.,
Gálvez José A.
Publication year - 2009
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.200900828
Subject(s) - chemistry , regioselectivity , moiety , bromide , stereochemistry , yield (engineering) , hydrochloride , ring (chemistry) , combinatorial chemistry , total synthesis , organic chemistry , catalysis , materials science , metallurgy
The asymmetric synthesis of (2 S ,3 R )‐2‐amino‐3‐octanedecanol hydrochloride (ES‐285 · HCl) was achieved in eight steps in ca. 38 % overall yield from the N ‐benzylimine‐derived from ( R )‐2,3‐ O ‐isopropylidene glyceraldehyde, which is easily available on gram scale from the inexpensive precursor D ‐mannitol. Highly diastereoselective addition of methylmagnesium bromide to the N ‐benzylimine was the key step to create the vic ‐amino alcohol moiety with the appropriate configuration. Regioselective ring opening of an intermediate aminoepoxide enabled the introduction of the long hydrocarbon chain at C4.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)