Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene–Claisen Rearrangement

Kenji Matsumoto; Naoyuki Mizushina; Masahiro Yoshida; Mitsuru Shindo

doi:10.1055/s-0036-1590970

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(17): 2340-2344
DOI: 10.1055/s-0036-1590970

letter

Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene–Claisen Rearrangement

Authors

Kenji Matsumoto*

^aFaculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihama-Boji, Yamashiro-cho, Tokushima 770-8514, Japan eMail: kmatsumoto@ph.bunri-u.ac.jp
Naoyuki Mizushina

^bInterdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1, Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan
Masahiro Yoshida

^aFaculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihama-Boji, Yamashiro-cho, Tokushima 770-8514, Japan eMail: kmatsumoto@ph.bunri-u.ac.jp
Mitsuru Shindo*

^cInstitute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan eMail: shindo@cm.kyushu-u.ac.jp

Abstract

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Abstract

We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene–Claisen rearrangement. The Claisen rearrangement of anti-allenyl alcohols provided (1E,3Z)-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels–Alder reactions are described.

Key words

allenes - Claisen rearrangement - conjugated dienes - bongkrekic acid - stereoselectivity

Volltext

Referenzen

References and Notes

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