Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam

Article Article scientifique Article Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam eng 2000-05-30 1997-02-03 author Von Oppolzer Wolfgang 25270 author Walther Eric Pierre Ernest 26676 author Perez Balado Juan Carlos 110194 author De Brabander Jef 30115 809-812 10.1016/s0040-4039(96)02408-2 0040-4039 https://linkinghub.elsevier.com/retrieve/pii/S0040403996024082 The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from N-propionylbornanesultament-2 yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6 → 7) followed by saponification of the sultam moiety (7 → 4) provided the Prelog-Djerassi lactonic acid 4 in a three step sequence in 61–71% overall yield. The Prelog-Djerassi lactonic acid 4 was synthesised in three steps (61–71% overall yield) starting from meso dialdehyde 5 utilizing a group-selective aldolization as a key step. Dewey 540 36 Département de chimie organique 141 false Tetrahedron letters 38 5 1625b550-2321-4c85-81cb-02690da0c098 Article (Published version) Restricted 1-s2.0-S0040403996024082-main.pdf 264194 application/pdf Vignette Public 1-s2.0-S0040403996024082-gr1.gif 6730 image/gif restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam	Tetrahedron letters			1997	173	0

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Perez Balado, Juan Carlos