An efficient catalyst-free Mukaiyama-aldol reaction of fluorinated enol silyl ethers with tryptanthrin

2015 ◽  
Vol 13 (33) ◽  
pp. 8906-8911 ◽  
Author(s):  
Fu-Min Liao ◽  
Yun-Lin Liu ◽  
Jin-Sheng Yu ◽  
Feng Zhou ◽  
Jian Zhou
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Aldol Reaction ◽  
Efficient Catalyst ◽  
Silyl Ethers ◽  
Mukaiyama Aldol Reaction ◽  
Catalyst Free ◽  
Mukaiyama Aldol ◽  
Enol Silyl Ethers ◽  
Fluoroalkyl Group

We report an efficient Mukaiyama-aldol reaction of tryptanthrin with fluorinated enol silyl ethers, which is carried out in methanol without the use of any catalyst. This represents the first modification of tryptanthrin by a fluoroalkyl group, which is applied to the total synthesis of the difluoro analogues of the natural product Phaitanthrin B.

Total Synthesis of Khafrefungin Using Highly Stereoselective Vinylogous Mukaiyama Aldol Reaction

2007 ◽  
Vol 9 (5) ◽  
pp. 849-852 ◽  
Author(s):  
Shin-ichi Shirokawa ◽  
Mariko Shinoyama ◽  
Isao Ooi ◽  
Seijiro Hosokawa ◽  
Atsuo Nakazaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

The Impact of the Mukaiyama Aldol Reaction in Total Synthesis

2013 ◽  
Vol 52 (35) ◽  
pp. 9097-9108 ◽  
Author(s):  
S. B. Jennifer Kan ◽  
Kenneth K.-H. Ng ◽  
Ian Paterson
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
The Impact

scholarly journals The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis

2014 ◽  
Vol 31 (4) ◽  
pp. 563-594 ◽  
Author(s):  
Markus Kalesse ◽  
Martin Cordes ◽  
Gerrit Symkenberg ◽  
Hai-Hua Lu
Keyword(s):  
Natural Product ◽  
Aldol Reaction ◽  
Natural Product Synthesis ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Recent Developments

This review will provide an overview on the recent developments of polyketide synthesis using the vinylogous Mukaiyama aldol reaction for the construction of advanced intermediates. In general, four different motifs can be constructed efficiently using the recent developments of asymmetric variants of this strategy.

scholarly journals Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A

Marine Drugs ◽  
2021 ◽  
Vol 19 (4) ◽  
pp. 198
Author(s):  
Tingrong Zhang ◽  
Shaojie Miao ◽  
Mingxiao Zhang ◽  
Wenjie Liu ◽  
Liang Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Scale Up ◽  
Scaling Up ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Cost Efficient

We have accomplished a 10-step (longest linear) total synthesis of nannocystin A on a four hundred milligram scale. The previously reported Kobayashi vinylogous Mukaiyama aldol reaction to connect C4 and C5 was unreproducible during the scaling up process. A more convenient and cost-efficient Keck asymmetric vinylogous aldol reaction was employed to improve this transformation.

scholarly journals Total Synthesis of Khafrefungin Using Highly Stereoselective Vinylogous Mukaiyama Aldol Reaction.

ChemInform ◽  
2007 ◽  
Vol 38 (30) ◽  
Author(s):  
Shin-ichi Shirokawa ◽  
Mariko Shinoyama ◽  
Isao Ooi ◽  
Seijiro Hosokawa ◽  
Atsuo Nakazaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

scholarly journals Total synthesis of the proposed structure of astakolactin

2014 ◽  
Vol 10 ◽  
pp. 2421-2427 ◽  
Author(s):  
Takayuki Tonoi ◽  
Keisuke Mameda ◽  
Moe Fujishiro ◽  
Yutaka Yoshinaga ◽  
Isamu Shiina
Keyword(s):  
Total Synthesis ◽  
Marine Sponge ◽  
Claisen Rearrangement ◽  
Aldol Reaction ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol

The first total synthesis of the proposed structure of astakolactin, a sesterterpene metabolite isolated from the marine sponge Cacospongia scalaris, has been achieved, mainly featuring Johnson–Claisen rearrangement, asymmetric Mukaiyama aldol reaction and MNBA-mediated lactonization.

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