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Asymmetric synthesis of (−)-denticulatins A and B via group-selective aldolization of a meso dialdehyde with a chiral N-propionylsultam

✍ Scribed by Wolfgang Oppolzer; Jef De Brabander; Eric Walther; Gérald Bernardinelli


Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
246 KB
Volume
36
Category
Article
ISSN
0040-4039

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The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from Npropionylbornanesultam ent-2 yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6 ---) 7) followed by saponification of the sultam moiety (7 --