- 1) a) McCann, P.A. and Pogell, B.M., Pamamycin: a new antibiotic and stimulator of aerial mycelia formation. J. Antibiot., 32, 673-678 (1979).
- b) Natsume, M., Yasui, K., Kondo, S., and Marumo, S., The structure of four new pamamycin homologs isolated from Streptomyces alboniger. Tetrahedron Lett., 32, 3087-3090 (1991).
- c) Natsume, M., Tazawa, J., Yagi, K., Abe, H., Kondo, S., and Marumo, S., Structure-activity relationship of pamamycins: effects of alkyl substituents. J. Antibiot., 48, 1159-1164 (1995).
- d) Recent review: Natsume, M., Study on bio-organic chemistry of aerial mycelium-differentiation in actinomycetes. Nippon Nogei Kagaku Kaishi (in Japanese), 72, 19-25 (1998).
- 2) a) Kondo, S., Yasui, K., Natsume, M., Katayama, M., and Marumo, S., Isolation, physico-chemical properties and biological activity of pamamycin-607, an aerial mycelium-inducing substance from Streptomyces alboniger. J. Antibiot., 41, 1196-1204 (1998).
- b) Kondo, S., Yasui, K., Katayama, M., Marumo, S., Kondo, S., and Hattori, H., Structure of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger. Tetrahedron Lett., 28, 5861-5864 (1987)
- c) Natsume, M., Kondo, S., and Marumo, S., The absolute stereochemistry of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger. J. Chem. Soc., Chem. Commun., 1911-1913 (1989).
- 3) Walkup, R.D. and Kim, Y.S., Synthesis of the C1-C14 subunit of macrodiolide antibiotics pamamycin-607 and pamamycin-635B. Tetrahedron Lett., 36, 3091-3094 (1995).
- 4) Mavropoulos, I. and Perlmutter, P., The total synthesis of pamamycin-607. 1. Synthesis of a C1'-C11' synthon. Tetrahedron Lett., 37, 3751-3754 (1996).
- 5) Mandville, G., Girald, C., and Bloch, R., A novel and efficient stereoselective synthesis of the southern fragment of pamamycin-607. Tetrahedron: Asymmetry, 8, 3665-3673 (1997).
- 6) Bernsmann, H., Hungerhoff, B., Fechner, R., Frohlich, R., and Metz, P., Toward the synthesis of pamamycin-607. Tetrahedron Lett., 41, 1721-1724 (2000).
- 7) Solladie, G., Salom-Roig, X.J., and Hanquet, G., Diastereodivergent synthesis of the C8-C18 precursor and C1'-C11' subunit of pamamycin-607 induced by a chiral sulfoxide group. Tetrahedron Lett., 41, 2737-2740 (2000).
- 8) Mandville, G. and Bloch, R., Towards the total synthesis of pamamycin-607: Preparation of the eastern fragment, (C8-C18 fragment). Eur. J. Org. Chem., 2303-2307 (1999).
- 9) Solladié, G., Salom-Roig, X.J., and Hanquet, G., Stereoselective synthesis towards the C8-C18 subunit of pamamycin-607 induced by a chiral sulfoxide group. Tetrahedron Lett., 41, 551-554 (2000).
- 10) Bernsmann, H., Frölich, R., and Metz, P., A sultone approach to the C(1)-C(18) moiety of pamamycin-607. Tetrahedron Lett., 41, 4347-4351 (2000).
- 11) Bernsmann, H., Gruner, M., and Metz, P., Enantioselective synthesis of the large fragment of pamamycin-607. Tetrahedron Lett., 41, 7629-7633 (2000).
- 12) Furuya, Y., Kiyota, H., and Oritani, T., Synthesis of the southern fragment of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger. Heterocycl. Commun., 6, 427-430 (2000).
- 13) Abe, M., Kiyota, H., Adachi, M., and Oritani, T., Synthesis of (±)-homononactic acid by using cis-selective iodoetherification. Synlett, 777-778 (1996).
- 14) Kiyota, H., Abe, M., Ono, Y., and Oritani, T., Synthesis of (+)-homononactic acid via iodoetherification. Synlett, 1093-1095 (1997).
- 15) Hanadate, T., Kiyota, H., and Oritani, T., Synthesis of (±)-methyl bishomononactate, a monomeric component of polynactic antibiotics. Biosci. Biotechnol. Biochem., 64, 1671-1674 (2000).
- 16) Idem., Synthesis of macrotetrolide a , a designed polynactin analog composed of (+)- and (-)-bishomononactic acids. Biosci. Biotechnol. Biochem., 65, 2118-2120 (2001).
- 17) a) Rychnovsky, S.D. and Bartlett, P.A., Stereocontrolled synthesis of cis-2.5-disubstituted tetrahydrofurans and cis- and trans-linalyl oxides. J. Am. Chem. Soc., 103, 3963-3964 (1981).
- b) Marek, I., Lefrançois, J.-M., and Normant, J.-F., Iodocyclization of olefinic t-butyl ethers: an easy stereocontrolled synthesis of cis-substituted tetrahydrofurans. Tetrahedron Lett., 33, 1747-1748 (1992).
- 18) Evans, D.A., Bartroli, J., and Shih, T.L., Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates. J. Am. Chem. Soc., 103, 2127-2129 (1981).
- 19) Rama Rao, A.V., Reddy, E.R., Joshi, B.V., and Yadav, J.S., Synthesis of (R)-1-benzyloxy-3-butene-2-ol a potential chiral synthon from L-(+)-tartaric acid: its applications in natural product synthesis. Tetrahedron Lett., 28, 6497-6500 (1987).
- 20) 13:[α]23 D-8.9° (c=0.52, CHCl3); lit., [α]25 D-6.95° (c=0.49, CHCl3), Mori, Y., Asai, M., Okumura, A., and Furukawa, H., Total synthesis of the polyene macrolide antibiotic roxaticin. 1. Synthesis of the polyol fragment of roxaticin using a four-carbon chain extension strategy. Tetrahedron, 51, 5299-5314 (1995).
- 21) 5 was converted from L-(-)-phenylalanine, [α]24 D+91.9° (c=1.09, EtOH); lit., [α]D+92.9° (c=1.01, EtOH), Gage, J.R. and Evans, D.A., Diastereoselective aldol condensation using a chiral oxazolidinone auxiliary(2S*,3S*)-3-hydroxy-3-phenyl-2-methylpropanoic acid. Org. Synth., Coll. Vol. VIII, 339-343 (1993).
Full access
Synthesis of Southern (C1'-C11') and Eastern (C8-C18) Fragments of Pamamycin-607, an Aerial Mycelium-inducing Substance of Streptomyces alboniger
Reprints and Corporate Permissions
Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?
To request a reprint or corporate permissions for this article, please click on the relevant link below:
Academic Permissions
Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?
Obtain permissions instantly via Rightslink by clicking on the button below:
If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.
Related research
People also read lists articles that other readers of this article have read.
Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.
Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.