Chiral Pool Synthesis: Starting from Terpenes

Gaich, Tanja; Mulzer, Johann

Comprehensive Chirality 2012, 2, 163-206.

In chiral pool syntheses, monoterpenes have found widespread application to gain access to a wide variety of acyclic and cyclic natural products. In the citronellol family, the chiral methyl branching has been found particularly useful. The monocyclic congeners such as carvone, pulegone, or phellandrene are obvious candidates for all kinds of ring annulations to form complex polycyclic structures. In this chapter, more than 40 representative natural product syntheses are described covering the time span from 1992 to 2011, four for citronellol, four for citronellal, two for citronellene, 12 for carvone, one for dihydrocarvone, 12 for pulegone, two for perillaldehyde, three for phellandrene, one for nepetalactone, and one for santonin, as chiral starting materials.