Simmons EJ,
Ryffel DB,
Lopez DA,
Boyko YD,
Sarlah D *.
Rice University, Houston and University of Illinois at Urbana−Champaign, Urbana, USA
Total Syntheses of Scabrolide B, Ineleganolide, and Related Norcembranoids.
J. Am. Chem. Soc. 2025;
147: 130-135
DOI:
10.1021/jacs.4c16629
Keywords
(–)-scabrolide B - nickel-mediated [3+2] annulation - Wittig homologation - Mukaiyama–Michael addition - Mukaiyama aldol reaction
Significance
Sarlah and co-workers report the total synthesis of (–)-scabrolide B. The authors chose a
convergent approach to the 5 /7 /6-norcembranoid-type natural product by
disconnecting the central seven-membered ring into fragment H and norcarvone
(I).
Comment
Starting from building block C, developed by the group of Sarlah in 2023, lactone H was synthesized in three steps. A sequence of Mukaiyama−Michael/aldol reactions gave access to the full carbon skeleton of the natural product in an efficient manner.
