Novel strategies to construct the γ-hydroxy lactone moiety of the CP molecules. Synthesis of the CP-225,917 core skeleton

Organic Letters

Volumn 1, Issue 1, 1999, Pages 63-66

  Nicolaou, K C ^a   He, Yun ^a   Fong, Kin Chiu ^a   Yoon, Won Hyung ^a   Choi, Ha Soon ^a   Zhong, Yong Li ^a   Baran, Phil S ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ENZYME INHIBITOR; LACTONE; MALEIC ANHYDRIDE; PHOMOIDRIDE A;

ARTICLE; CHEMISTRY; CONFORMATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

ENZYME INHIBITORS; INDICATORS AND REAGENTS; LACTONES; MALEIC ANHYDRIDES; MOLECULAR CONFORMATION; OXIDATION-REDUCTION;

EID: 0033564995     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990551y     Document Type: Article

References (39)

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20. The synthesis of 3 via a route similar, yet superior, to that reported in ref 2a will be reported in due course.
21. All new compounds were fully characterized spectroscopically.
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27. The use of high-dilution syringe pump techniques and even alternative initiators/reductants could not reduce the amount of this byproduct.
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32. 7 (5.0 equiv) was then added without rigorous removal of trace acid (no base added). The reaction could be easily monitored by TLC, with formation of intermediate lactol 14 after only a few minutes. DMP (5.0 equiv) was added, and stirring was continued for 12-16 h at 25 °C to furnish bis-lactol 17 in 82% yield after column chromatography.
33. 4, Jones, and TPAP were among the reagents tried.
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39. Due to space limitations, details will be provided in a full account of this work.