Expedient access to enantiopure cyclopentanic natural products: total synthesis of (-)-cyclonerodiol.
Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).
Carmen
C
Pérez Morales
M
M
Mar Herrador
José F
JF
Quílez del Moral
Alejandro F
AF
Barrero
D000080462:Acyclic Monoterpenes; D003517:Cyclopentanes / Q000138:chemical synthesis; D005240:Feasibility Studies; D039821:Monoterpenes / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013729:Terpenes / Q000138:chemical synthesis*
D000080462:Acyclic Monoterpenes; D003517:Cyclopentanes; D039821:Monoterpenes; D012717:Sesquiterpenes; D013729:Terpenes; C104104:plinol; C000539:cyclonerodiol; C018584:linalool