New strategies for the synthesis of biologically important tetrapyrroles. The "B,C+D+A" approach to linear tetrapyrroles

New strategies for the synthesis of biologically important tetrapyrroles. The "B,C+D+A" approach to linear tetrapyrroles
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DOI:
10.1021/jo991503u
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发表时间:
2000-01-14
影响因子:
3.6
通讯作者:
Leung, SH
Leung, SH
中科院分区:
化学2区
文献类型:
--
作者:
Jacobi, PA;Coutts, LD;Leung, SH

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通过一种新的策略以对映体专一性的方式合成了与光敏色素(1)相关的线性四吡咯,该策略始于19型的环-B,C合成子(双碘联吡咯)。通过Pd(0)介导的19a与适当的炔酸或酰胺衍生物9和20的偶联,然后分子内环化(方法C:BC+D+A->ABCD)来阐述环A和D。
Linear tetrapyrroles related to phytochrome (1) were prepared in enantiospecific fashion by a new strategy beginning with ring-B,C synthons of type 19 (bis-iododipyrrins). Rings A and D were elaborated by Pd(0)-mediated coupling of 19a with the appropriate alkyne acid or amide derivatives 9 and 20, followed by intramolecular cyclization (method C: BC + D + A --> ABCD).