Facile synthesis of the enantiomers of frontalin

1984 ◽  
Vol 62 (11) ◽  
pp. 2148-2154 ◽  
Author(s):  
B. D. Johnston ◽  
A. C. Oehlschlager
Keyword(s):  
Asymmetric Epoxidation ◽  
Facile Synthesis ◽  
Epoxidation Reaction ◽  
Synthetic Sequence ◽  
Sharpless Asymmetric Epoxidation

S-(−)- and R-(+)-frontalin (1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane) were prepared from (E)-2-methyl-2,6-heptadiene-1-ol utilizing the Sharpless asymmetric epoxidation reaction to induce chirality. The six-step synthetic sequence proceeded in approximately 50% overall yield and was found to be suitable for the preparation of multi-gram quantities of either enantiomer with ≥ 90% ee.

Stereo-Controlled Total Synthesis of Ieodomycins A and B

2014 ◽  
Vol 881-883 ◽  
pp. 57-60 ◽  
Author(s):  
Cheng Lin Zhu ◽  
Jian Ting Zhang ◽  
Shi Peng Chen ◽  
Jun Min Feng ◽  
Gao Peng Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Aldol Reaction ◽  
Asymmetric Epoxidation ◽  
Formal Synthesis ◽  
Mukaiyama Aldol ◽  
Synthetic Sequence ◽  
Key Features ◽  
Swern Oxidation ◽  
Sharpless Asymmetric Epoxidation

A highly convergent formal synthesis of Ieodomycins A and B was achieved in 7 steps. The key features involved in the synthetic sequence of Ieodomycins A and B are the Sharpless asymmetric epoxidation and the Mukaiyama aldol reaction[. The synthesis of C-3 epimer of Ieodomycins A and B was also accomplished in good yields, but now just Heptyl diene aldehyde was getted thought 4 steps. Use Geraniol as meterials to make the corresponding aldehyde (1) via Swern oxidation. Though epoxidation, Wittig reaction and HIO4oxidation to get the intermediate . Useing it though few steps, the target molecule can be getted.

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