Studies on synthesis of optically active twelve-membered diynes: a convergent construction of a twelve-membered diketodiyne compound with C-2 symmetry

Citation
C. Mukai et al., Studies on synthesis of optically active twelve-membered diynes: a convergent construction of a twelve-membered diketodiyne compound with C-2 symmetry, J CHEM S P1, (5), 2000, pp. 737-744
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
5
Year of publication
2000
Pages
737 - 744
Database
ISI
SICI code
0300-922X(2000):5<737:SOSOOA>2.0.ZU;2-0
Abstract
A convergent procedure for the preparation of optically active twelve-membe red diketodiyne derivatives with C-2 symmetry possessing four hydroxy funct ionalities was developed starting from the commercially available diethyl L -tartrate. The key step for the construction of the twelve-membered diyne f ramework involved an intramolecular chromous chloride-mediated coupling rea ction between the aldehyde functionality and the alkyne moiety having an io dine atom at its terminus.