Synthetic study on naturally occurring acetylenic spiroacetal enol ethers:The first access to optically active 3,4-diacetoxy-2-formylmethylene-1,6-dioxaspiro[4.5]decanes

Authors
Toshima, H Aramaki, H Ichihara, A
Citation
H. Toshima et al., Synthetic study on naturally occurring acetylenic spiroacetal enol ethers:The first access to optically active 3,4-diacetoxy-2-formylmethylene-1,6-dioxaspiro[4.5]decanes, TETRAHEDR L, 40(18), 1999, pp. 3587-3590
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
18
Year of publication
1999
Pages
3587 - 3590
Database
ISI
SICI code
0040-4039(19990430)40:18<3587:SSONOA>2.0.ZU;2-G
Abstract
Optically active 3,4-diacetoxy-2-formylmethylene-1,6-dioxaspiro[4.5]decanes have been synthesized from an acyclic keto-alcohol possessing an unsaturat ed aldehyde part via intramolecular conjugate addition. The C3- and C4-ster eogenic centers were introduced via Sharpless asymmetric dihydroxylation of an acyclic conjugated ketone with modified AD-mix-alpha in high enantiosel ectivity (96% e.e.). This is the first access to optically active spiroacet al 2-enol ethers. (C) 1999 Elsevier Science Ltd. All rights reserved.