Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B.

Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B.
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毒蛙生物碱 251O 和反式 223B 的高效对映和非对映发散合成。

DOI:
10.1021/jo901100m
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发表时间:
2009
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Daly,JohnW
Daly,JohnW
中科院分区:
--
文献类型:
--
作者:
Toyooka,Naoki;Zhou,Dejun;Nemoto,Hideo;Tezuka,Yasuhiro;Kadota,Shigetoshi;Andriamaharavo,NirinaR;Garraffo,HMartin;Spande,ThomasF;Daly,JohnW

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本文报道了一种以普通内酰胺为起始原料,采用对映体分散法合成毒蛙生物碱251 O和反式-223 B的方法。251 O和反式-223 B的相对立体化学分别为7(R = n-C7 H 15,R′ =n-Pr)和14。
An efficient and flexible synthesis of poison-frog alkaloids251Oandtrans-223Bhas been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam1. The relative stereochemistry of251Oandtrans-223Bwas determined to be7(R =n-C7H15, R′ =n-Pr) and14by the present enantioselective synthesis.