Canadian Journal of Chemistry

Five-membered ring spiro-annulation via thermal rearrangement of enol silyl ethers of 2-(cyclopropylmethylene) cycloalkanones. A formal total synthesis of some …

E Piers, CK Lau, I Nagakura

Index: Piers, Edward; Lau, Cheuk Kun; Nagakura, Isao Canadian Journal of Chemistry, 1983 , vol. 61, p. 288 - 297

Full Text: HTML

Citation Number: 18

Abstract

Treatment of the 2-(iodomethylene) cycloalkanones 10 and 11 with lithium (phenylthio)( cyclopropyl) cuprate provided good yields of the corresponding β-cyclopropyl enones 12 and 13, respectively. Thermolysis of the latter substances produced relatively poor yields of the desired spiro-annulation products 14 and 15. However, conversion of 12 and 13 into the corresponding enol silyl ethers 24 and 25, followed by thermal rearrangement of the latter ...

 Related Synthetic Route

~10%

Learn More

~%

Learn More

~%

Learn More

~44%

Learn More

~%

Learn More

~%

Learn More

~%

Learn More

~28%

Learn More

~%

Learn More

~26%

Learn More

~%

Learn More

~%

Learn More

~%

Learn More

~%

Learn More

~%

Learn More

~%

Learn More

~%

Learn More

~%

Learn More

~%

Learn More

~%

Learn More