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Synthesis of 3α-hydroxy -5β,10β-epoxychiliolide, an isolabdane derivative from chiliotrichium rosmarinifolium

✍ Scribed by C. Harde; F. Bohlmann

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
677 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis

Starting with CI-methoxytetralone the unusual diterpene Sahydroxy-5&10,3-epoxychiliolide (l5a) has been synthesized vk methyl-[lcu,2a]-l',2,3,4,5,6,7,8-ocCahydro-6-oxo-l-g-propenyl)-~,5-trimethyl-1-naphthoate (9) which by boranate reduction gave the desired o-hydroxy derivative.-Oxidative degradatlon of the propenyl side chain afforded the aldehyde llr which could be transformed to the racemic furan diterpene 15a byxaction with 3-lithiumfuran followed by lactonization and epoxidafion. Similar the epimeric compounds z, 15~ and 15d were synthesized which allowed a final proof of the proposxrelative ZEreochemistry of the six chiral centres of the natural compound.

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