We thank Prof. M. Suzuki (Hokkaido University) for providing the spectra of itomanallene A and neolaurallene. We are grateful to Dr. H. C. Ahn (KIST) for the measurement of 900 MHz 1H NMR spectra of 3 c and ent-2. This work was supported by the SRC/ERC program of MOST/KOSEF (R11-2007-107-00000-0).
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Communication
Substrate-Controlled Asymmetric Total Synthesis and Structure Revision of (+)-Itomanallene A†
Article first published online: 22 DEC 2009
DOI: 10.1002/anie.200905826
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Jeong, W., Kim, M., Kim, H., Kim, S., Kim, D. and Shin, K. (2010), Substrate-Controlled Asymmetric Total Synthesis and Structure Revision of (+)-Itomanallene A. Angewandte Chemie International Edition, 49: 752–756. doi: 10.1002/anie.200905826
- †
Publication History
- Issue published online: 13 JAN 2010
- Article first published online: 22 DEC 2009
- Manuscript Received: 16 OCT 2009
Funded by
- MOST/KOSEF. Grant Number: R11-2007-107-00000-0
Keywords:
- alkylation;
- natural products;
- structure elucidation;
- total synthesis
Graphical Abstract
In control: The first asymmetric total synthesis of (+)-itomanallene A (revised structure) has been accomplished starting from commercially available (S)-glycidol in a substrate-controlled fashion. The approach yields α,α′-cis- or α,α′-trans-tetrahydrofuran isomers by intramolecular alkylation with either an amide enolate or a nitrile anion, respectively.