Dioxolane-to-bridged acetal-to-spiroketal via ring-closing metathesis and rearrangement: a novel route to 1,7-dioxaspiro[5.5]undecanes.
Org Lett
; 4(3): 467-70, 2002 Feb 07.
Article
in En
| MEDLINE
| ID: mdl-11820906
Several examples of 1,7-dioxaspiro[5.5]undecane spiroketal systems have been synthesized from the common bicyclic intermediate 1 via acid-catalyzed rearrangement. Intermolecular ketalization of C(2) symmetric diene diol 3 with ketone 9 and then desymmetrization by ring-closing metathesis rapidly constructs bicyclic acetal 1. The locked conformation and steric bias of 1 allow stereoselective functionalization of one or both double bonds before spiroketalization.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Dioxolanes
/
Alkanes
/
Acetals
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2002
Document type:
Article
Affiliation country:
United States
Country of publication:
United States