Problem: Crude extracts from the ginkgo tree, Ginkgo biloba, have been used for centuries to alleviate symptoms associated with asthma. There are four principal components of Ginkgo extracts, called ginkgolide A, B, D, and M. During E. J. Corey’s classic synthesis of ginkgolide B, compound  1 was converted into compound 5 (J. Am. Chem. Soc. 1988, 110, 649–651): (b) Draw a mechanism for the conversion of  1 to 3 and explain why this step is irreversible.

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Crude extracts from the ginkgo tree, Ginkgo biloba, have been used for centuries to alleviate symptoms associated with asthma. There are four principal components of Ginkgo extracts, called ginkgolide A, B, D, and M. During E. J. Corey’s classic synthesis of ginkgolide B, compound  1 was converted into compound 5 (J. Am. Chem. Soc. 1988, 110, 649–651):

(b) Draw a mechanism for the conversion of  1 to 3 and explain why this step is irreversible.

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Based on our data, we think this problem is relevant for Professor Reynolds' class at GT.

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 2nd Edition. You can also practice Organic Chemistry - Klein 2nd Edition practice problems.