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. 2006 Mar 1;128(8):2604-8.
doi: 10.1021/ja057433s.

Enantioselective total synthesis of batzelladine F and definition of its structure

Frederick Cohen  1 , Larry E Overman
Affiliations

Enantioselective total synthesis of batzelladine F and definition of its structure

Frederick Cohen et al. J Am Chem Soc. .

Abstract

Batzelladine F (1) was synthesized in enantioselective and stereoselective fashion in 15 steps (longest linear sequence) and 1.7% overall yield from two readily available enantioenriched beta-hydroxy esters, methyl (R)-3-hydroxydecanoate and methyl (R)-3-hydroxybutyrate. Tethered Biginelli condensations are used to assemble both tricyclic guanidine fragments, with the second tethered Biginelli condensation (14 + 16 --> 17) also being employed to join the guanidine fragments. Three diastereomers of batzelladine F, 2-4, were prepared also. A combination of HPLC, optical rotation and CD spectroscopy was employed to distinguish stereoisomers 1-4, proving that 1 is the correct structure of the hexacyclic marine alkaloid batzelladine F.

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Figures

Figure 1
Figure 1
Eight possibilities for the revised structure of batzelladine F.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Figure 2
Figure 2
CD spectra of the ditrifluoroacetate salts of authentic batzelladine F (0.3 mg/mL), and synthetic products 1 (3.9 mg/mL) and 2 (3.6 mg/mL) in MeOH.
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References

    1. Current Address: Department of Medicinal Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080.

    1. Patil AD, Freyer AJ, Taylor PB, Carté B, Zuber G, Johnson RK, Faulkner DJ. J. Org. Chem. 1997;62:1814–1819.

    1. For reviews summarizing the isolation, structure and synthesis of batzelladine alkaloids, see: Berlinck RGS, Kossuga MH. J. Nat. Prod. 2005;22:516–550. and earlier reviews in this series. For the recent isolation of a new batzelladine alkaloid, see: Gallimore WA, Kelly M, Scheuer PJ. J. Nat. Prod. 2005;68:1420–1423. For a recent synthetic study, see: Arnold MA, Duron SG, Gin DY. J. Am. Chem. Soc. 2005;127:6924–6925.

    1. Cohen F, Overman LE. preceding contribution in this issue.

    1. As discussed in detail in the preceding article, the relative configuration originally proposed for the right-hand tricyclic guanidine fragment of batzelladine F had been revised by the synthesis of model compounds.,

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