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Dermostatin A

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Dermostatin A
Category Antibiotics
Catalog number BBF-01832
CAS 51053-36-2
Molecular Weight 720.93
Molecular Formula C40H64O11

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Streptomyces viridogriseus. Dermostatin A has the activity of resisting yeast, aspergillus Niger, Mosses and histoplasma capsulatum, etc.

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Synonyms BRN 1417386
IUPAC Name (3E,5E,7E,9E,11E,13E,16S,17S,18R,20R,22R,24S,26S,28R,30R,32R,33E,35S,36S)-16,18,20,22,24,26,28,30,32-nonahydroxy-17,35-dimethyl-36-propan-2-yl-1-oxacyclohexatriaconta-3,5,7,9,11,13,33-heptaen-2-one
Canonical SMILES CC1C=CC(CC(CC(CC(CC(CC(CC(CC(C(C(CC=CC=CC=CC=CC=CC=CC(=O)OC1C(C)C)O)C)O)O)O)O)O)O)O)O
InChI InChI=1S/C40H64O11/c1-27(2)40-28(3)18-19-30(41)20-31(42)21-32(43)22-33(44)23-34(45)24-35(46)25-36(47)26-38(49)29(4)37(48)16-14-12-10-8-6-5-7-9-11-13-15-17-39(50)51-40/h5-15,17-19,27-38,40-49H,16,20-26H2,1-4H3/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,19-18+/t28-,29-,30-,31-,32-,33+,34-,35+,36+,37-,38+,40-/m0/s1
InChI Key LSYAYTGVPHMMBZ-YPCSGYANSA-N
Appearance Yellow Long Filamentous Crystalline
Antibiotic Activity Spectrum fungi; yeast
1. Total synthesis of dermostatin A
Yingchao Zhang, Carolynn C Arpin, Aaron J Cullen, Mark J Mitton-Fry, Tarek Sammakia J Org Chem. 2011 Oct 7;76(19):7641-53. doi: 10.1021/jo2012658. Epub 2011 Sep 15.
The concise total synthesis of dermostatin A is described. Highlights include a two-directional application of the asymmetric acetate aldol method developed in our lab, a novel diastereotopic-group-selective acetal isomerization for terminus differentiation, and a selective cross-metathesis reaction between a terminal olefin and a trienal. A study of the scope and viability of similar cross-metathesis reactions is also described. The synthesis is convergent and utilizes fragments of roughly equal complexity.
2. Two-directional desymmetrization by double 1,4-addition of silicon and boron nucleophiles
Eduard Hartmann, Martin Oestreich Org Lett. 2012 May 4;14(9):2406-9. doi: 10.1021/ol300832f. Epub 2012 Apr 16.
The two-directional desymmetrization of prochiral precursors with α,β-unsaturated branches by catalyst-controlled 1,4-addition of silicon and likewise boron nucleophiles allows for a general enantioselective access to syn,anti-triols with 1,n + 1,2n + 1 (n = 2 and 3) substitution patterns. The utility is demonstrated in the synthesis of the C17-C25 fragment of dermostatin A.
3. Total Synthesis of Dermostatin A
Christopher J Sinz, Scott D Rychnovsky Angew Chem Int Ed Engl. 2001 Sep 3;40(17):3224-3227. doi: 10.1002/1521-3773(20010903)40:173.0.CO;2-D.
An oxo-hexaene macrolide antibiotic, dermostatin A has been synthesized. Key features of the synthesis include the application of cyanohydrin acetonide couplings for the synthesis of the polyol portion, and the convergent introduction of the polyene segment by means of a Stille coupling.

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