RT Journal Article
T1 Concise, enantioselective, and versatile synthesis of (−)-Englerin A Based on a platinum-catalyzed [4C+3C] cycloaddition of allenedienes
A1 Nelson, Ronald
A1 Gulías Costa, Moisés
A1 Mascareñas Cid, José Luis
A1 López García, Fernando
K1 Englerin-A
K1 Achiral precursors
K1 Cycloaddition
K1 Allenes
K1 Asymmetric catalysis
K1 Guaiane natural products
K1 Total synthesis
AB A practical synthesis of (−)-englerin A was accomplished in 17 steps and 11 % global yield from commercially available achiral precursors. The key step consists of a platinum-catalyzed [4C+3C] allenediene cycloaddition that directly delivers the trans-fused guaiane skeleton with complete diastereoselectivity. The high enantioselectivity (99 % ee) stems from an asymmetric ruthenium-catalyzed transfer hydrogenation of a readily assembled diene–ynone. The synthesis also features a highly stereoselective oxygenation, and a late-stage cuprate alkylation that enables the preparation of previously inaccessible structural analogues
PB WILEY-VCH Verlag GmbH
YR 2016
FD 2016-10-13
LK http://hdl.handle.net/10347/15018
UL http://hdl.handle.net/10347/15018
LA eng
NO R. Nelson, M. Gulías, J. L. Mascareñas, F. López, Angew. Chem. Int. Ed. 2016, 55, 14359
NO NOTICE: This is the peer reviewed version of the following article: Ronald Nelson, Moisés Gulías, José L. Mascareñas*, Fernando López* (2016), A Concise, Enantioselective and Versatile Synthesis of (-)-Englerin A based on a Pt-catalyzed [4C+3C] Cycloaddition of Allenedienes, Angew. Chem. Int. Ed., 55, 1-6 [doi:10.1002/anie.201607348]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving
NO Support by the Spanish MINECO (SAF2013-41943-R), ERDF, ERC (Adv. Grant 340055), Xunta de Galicia (GRC2013-041 and 2015-CP082), Orfeo-cinqa CTQ2014-51912-REDC, and CONICYT-Becas Chile (grant to R.N.) is gratefully acknowledged. Dr. Isaac Alonso is acknowledged for preliminary contributions
DS Minerva
RD 24 abr 2026