cas 52665-69-7, A23187 | Articles data ｜lookchem

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52665-69-7

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Stereocontrolled Total Synthesis of Antibiotic A-23187 (Calcimycin)
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Martinez, Gregory R.,Grieco, Paul A.,Williams, Eric,Kanai, Ken-ichi,Srinivasan, C. V.
p. 1436 - 1438
(1982)
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A TOTAL SYNTHESIS OF POLYETHER ANTIBIOTIC (-)-A23187 (CALCIMYCIN)
A total synthesis of (-)-A23187 (calcimycin) was accomplished by a convergent approach.The key step of synthesis was the stereospecific cyclization of the β-hydroxy ketone into the spiroketal under basic conditions.
Negri, David P.,Kishi, Yoshito
p. 1063 - 1066
(1987)
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The chemistry of cyclic vinyl ethers. 6. Total synthesis of polyether ionophore antibiotics of the calcimycin (A-23187) class
An extremely convergent (longest linear sequence, 16 steps), fully stereoselective, and potentially general synthesis of the antibiotic ionophores of the Calcimycin (A-23187) class was devised. The key steps involve a coupling reaction between the chiral nonracemic subunits dihydropyran 41 (as the α-lithio anion) and bromide 49. Subsequent acid-promoted cyclization directly produces the spirocyclic ring system found in the ionophore X-14885A (3). Alternatively, cyclopropanation of substituted vinyl ether 55 followed by acid treatment afforded the spiroketal 58 that was subsequently converted into the polyether ionophore Calcimycin (1) and also Cezomycin (2).
Boeckman Jr., Robert K.,Charette, André B.,Asberom, Theodros,Johnston, Brian H.
p. 5337 - 5353
(2007/10/02)

A Convergent General Synthetic Protocol for Construction of Spirocyclic Ketal Ionophores: An Application to the Total Synthesis of (-)-A-23187 (Calcimycin)
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Boeckman, Robert K. Jr.,Charette, Andre B.,Asberom, Theodros,Johnston, Brian H.
p. 7553 - 7555
(2007/10/02)

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Chemical Properties

Melting Point: 187-190?°C
Boiling Point: 710.3±55.0 °C(Predicted)
Flash Point:383.391oC
Density: 1.28±0.1 g/cm3(Predicted)
Solubility:Soluble in DMSO with warming or sonication. Also soluble in etha
Storage Temp.:2-8°C
PKA: pKa1 6.9 in 90% DMSO
Merck: 13,1639
BRN: 1096801
PSA: 126.68000
LogP: 5.60280

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