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Aldol reactions of methyl 2-methoxypropanoate (4), the corresponding ester of 2-methoxypropanoic acid with 4-methyl-2,6di-(rert-butyl)phenol(l3), and silylketene acetals 14 and 15 with (S)-2-(phenylmethoxy)propanal(l7) have been investigated. The lithium enolate of 4 reacts with 17 to give primarily Bhydroxy ester lga. If the reaction is carried out with the bis-silylketene acetal 14 under the influence of stannic chloride, B-hydroxy acid 2Ck is produced. Compound 2Oe is cleanly inverted, via the p-lactone 26, to provide &hydroxy acid 19~. Compound l&s has been converted into L-cladinose by the sequence of steps: 18r+35-+39+40-+41+42~1. \* Paper 49 in the series "Acyclic Stereoselection". For naoer 48. see ref. 1. ' To-whom inquiries shouldbe addressed. \_ \_ \* For a preliminary communication, see ref. 3. \*\* Ref. 4(a) records a recent synthesis of (-)-cladinose. For previous synthesis of cladinose and reiated branched-chain sugars, see ref. 4b. OOOS-6215/90/%03.50 @ 1990 Elsevier Science Publishers B.V. 'BuPh$iO Schmmo 2 12 dependent on the base used in the deprotonation. With lithium 2,2,6$Gtetramethylpiperidide (LTMP) in THF, or with lithium diisopropylamide (LDA) in a mixture

Author

Stephen H. Montgomery; Michael C. Pirrung; Clayton H. Heathcock

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1990

Language

EN