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. 2012 Mar 16;14(6):1596-9.
doi: 10.1021/ol300342n. Epub 2012 Feb 28.

Expedient enantioselective synthesis of cermizine D

Nagarathanam Veerasamy  1 , Erik C Carlson, Rich G Carter
Affiliations

Expedient enantioselective synthesis of cermizine D

Nagarathanam Veerasamy et al. Org Lett. .

Abstract

An efficient enantioselective synthesis of cermizine D has been developed that exploits the use of a common intermediate to access over 85% of the carbon backbone. Key steps include an organocatalyzed heteroatom Michael addition, a diastereoselective alkylation with α-iodomethyl phenyl sulfide, a conjugate addition to a vinyl sulfone species, and a sulfone coupling/desulfurization sequence to join the two major subunits.

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Figures

Figure 1
Figure 1
ORTEP Representation of the X-Ray Crystallographic Data of Compound 15.
Scheme 1
Scheme 1
Retrosynthetic Analysis.
Scheme 2
Scheme 2
Synthesis of Common Intermediate.
Scheme 3
Scheme 3
Synthesis of Sulfone Fragment.
Scheme 4
Scheme 4
Improved Routes to Sulfone Fragment.
Scheme 5
Scheme 5
Completion of the Synthesis.
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