Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 16, Pages 2903-2910Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1500-1407
Keywords
bis-THF C-15 acetogenins; carbohydrate building block; Sharpless asymmetric dihydroxylation-cycloetherification; S(N)2 halogenation; relay-cross-metathesis
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Funding
- CSIR
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This paper describes a highly diastereoselective total synthesis of several bis-THF C-15 acetogenin natural products, as well as the synthesis of an advanced intermediate reported in the total synthesis of (E/Z)-elatenynes. Key features in the synthesis include epoxide opening, Birch reduction, Sharpless asymmetric dihydroxylation-cycloetherification, S(N)2 halogenation, and a relay cross metathesis.
A highly diastereoselective total synthesis of several bis-THF C-15 acetogenin natural products, chloroenyne from Laurencia majuscula, laurendecumenyne B, and laurefurenyries A/B, is reported. Additionally the synthesis of an advanced intermediate reported in the earlier total synthesis of (E/Z)-elatenynes (formal synthesis) is described. The salient features in the synthesis include epoxide opening, Birch reduction, Sharpless asymmetric dihydroxylation-cycloetherification, S(N)2 halogenation, and a relay cross metathesis.
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