?

Organic Chemistry 2

Free Version

Upgrade subject to access all content

Difficult

Alpha Carbonyl Chemistry: Robinson Annulation

ORGO2-SYFOXB

The Wieland–Miescher (W.M.) ketone is a very useful compound used for the construction of a variety of biologically active compounds, including steroids and terpenoids. It is also used for the synthesis of the anti-cancer drug called taxol (Ref. 1).

The structure of the W.M. ketone is as shown below. It can be synthesized by the Robinson annulation reaction.

Based on your knowledge of the Robinson annulation reaction, which of the following options is the correct choice of the reagents to make the W.M. ketone?

Created for Albert.io. Copyright 2016. All rights reserved.

Ref. 1: Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder,​ L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. Total Synthesis of Baccatin III and Taxol. J. Am. Chem. Soc. 1996, 118, 2843−2859.

A

Created for Albert.io. Copyright 2016. All rights reserved.

B

Created for Albert.io. Copyright 2016. All rights reserved.

C

Created for Albert.io. Copyright 2016. All rights reserved.

D

Created for Albert.io. Copyright 2016. All rights reserved.