Bistramide A

Bistramide A

Identifiers
ChEMBL	ChEMBL1221600
ChemSpider	25053776
Jmol interactive 3D	Image
InChI InChI=1S/C40H68N2O8/c1-8-11-32(44)23-34-17-15-27(3)37(48-34)24-38(46)42-25-35(45)30(6)39(47)41-21-10-13-36-28(4)18-20-40(50-36)19-9-12-33(49-40)16-14-26(2)22-29(5)31(7)43/h8,11,22,26-28,30-31,33-37,43,45H,9-10,12-21,23-25H2,1-7H3,(H,41,47)(H,42,46)/b11-8+,29-22+/t26-,27-,28-,30-,31-,33+,34+,35-,36+,37-,40-/m0/s1 Key: HXZRMADPDYFMEB-FTTMEYFSSA-N InChI=1/C40H68N2O8/c1-8-11-32(44)23-34-17-15-27(3)37(48-34)24-38(46)42-25-35(45)30(6)39(47)41-21-10-13-36-28(4)18-20-40(50-36)19-9-12-33(49-40)16-14-26(2)22-29(5)31(7)43/h8,11,22,26-28,30-31,33-37,43,45H,9-10,12-21,23-25H2,1-7H3,(H,41,47)(H,42,46)/b11-8+,29-22+/t26-,27-,28-,30-,31-,33+,34+,35-,36+,37-,40-/m0/s1 Key: HXZRMADPDYFMEB-FTTMEYFSBD
SMILES C\C=C\C(=O)C[C@H]1CC[C@H](C)[C@H](CC(=O)NC[C@H](O)[C@H](C)C(=O)NCCC[C@H]2O[C@@]3(CCC[C@H](CC[C@H](C)\C=C(/C)\[C@H](C)O)O3)CC[C@@H]2C)O1
Properties
Chemical formula	C40H68N2O8
Molar mass	704.99 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Bistramide A is a chemical compound originally found in the marine ascidian Lissoclinum bistratum.

It was found that the cyclic portion of the synthesis proceeds through a Petkov transition-state model followed by an asymmetric [4+2] Robinson annulation into the desired diamide product.

A more efficient crystallization was further described by J. Job, M.D., where a Kalmanson catalyst is used to quickly build up and break down the Petkov transition-state, followed by a Berne backside attack, which instantaneously causes the precipitation of the product.

References