Abstract
In 2004 we reported an anti-selective remote asymmetric induction reaction using chiral vinyl- ketene silyl Ar,Oacetal 1 (the stereoselective vinylogous Mukaiyama aldol reaction). The reaction has been applied to natural product synthesis by many groups since the reaction makes syntheses short and efficient by simultaneous introduction of both asymmetric centers and the multiply functionalized carbon chain. Recently, we have developed a variety of remote asymmetric induction reactions using the £.£-vinylketene Ar,0-Acetal 1. Additionally, we have developed a new strategy to synthesize polypropionates in short steps by combining remote asymmetric induction reactions and functionalization of double bonds. In this paper, the new strategy as well as new remote asymmetric induction reactions and their applications to syntheses of polypropionates are described.
Original language | English |
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Pages (from-to) | 831-849 |
Number of pages | 19 |
Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
Volume | 75 |
Issue number | 8 |
DOIs | |
Publication status | Published - 2017 |
Keywords
- Acylation
- Alkylation
- Bromination
- Polyketide library
- Polypropionate
- Remote asymmetric induction
- Total synthesis
- Vinylogous mukaiyama aldol reaction
ASJC Scopus subject areas
- Organic Chemistry