@article {5150,
	title = {Sugar-pendant diamines},
	journal = {Journal of Organic Chemistry},
	volume = {66},
	number = {11},
	year = {2001},
	note = {ISI Document Delivery No.: 435ZDTimes Cited: 19Cited Reference Count: 62},
	month = {Jun},
	pages = {3783-3789},
	type = {Article},
	abstract = {A set of 1,3-propanediamine derivatives connected to carbohydrates (5) has been prepared in four steps from peracetylated sugar and 1,3-dibromo-2-propanol in 60-73\% yields. D-Glucose, D-mannose, D-galactose, D-xylose, D-ribose, and maltose are utilized as sugar molecules in this work. The diamine moiety was connected to the C1 carbon of the glycopyranose ring via an O-glycoside bond. All of the anomeric configurations and sugar puckering conformations, except in the D-maltose derivative, were determined by X-ray crystallography of the diazido or dibromo precursors. While glycosidation of peracetylated galactopyranose with 1,3-dibromo-2-propanol in the presence of boron trifluoride afforded both anomers, the neighboring group participation of the 2-acetoxy group yielded a single anomer for the other substrates. This method has been used to synthesize a library of sugar-pendant diamines including an OH-protected derivative (6), and an N,N {\textquoteright} -diisopropyl-substituted derivative (7). A similar series of reactions using 2,3-dibromo-1-propanol gave ethylenediamine-type derivatives (11), and bis(bromomethyl)bis(hydroxymethyl)methane (12) gave bisglucose-pendant derivatives (16).},
	keywords = {BINDING-PROPERTIES, C-2 EPIMERIZATION, CARBON SKELETON, D-GLUCOSE, ETHYLENEDIAMINE, LIGANDS, N-GLYCOSIDES, NICKEL(II) COMPLEXES, PHOTOCYTOTOXICITY, WATER},
	isbn = {0022-3263},
	url = {<Go to ISI>://000168911300018},
	author = {Mikata, Y. and Shinohara, Y. and Yoneda, K. and Nakamura, Y. and Esaki, K. and Tanahashi, M. and Brudzinska, I. and Hirohara, S. and Yokoyama, M. and Mogami, K. and Tanase, T. and Kitayama, T. and Takashiba, K. and Nabeshima, K. and Takagi, R. and Takatani, M. and Okamoto, T. and Kinoshita, I. and Doe, M. and Hamazawa, A. and Morita, M. and Nishida, F. and Sakakibara, T. and Orvig, Chris and Yano, S.}
}
@article {4034,
	title = {Investigations of terpenoid biosynthesis by the dorid nudibranch Cadlina luteomarginata},
	journal = {Journal of Organic Chemistry},
	volume = {62},
	number = {21},
	year = {1997},
	note = {ISI Document Delivery No.: YC657Times Cited: 16Cited Reference Count: 21},
	month = {Oct},
	pages = {7239-7246},
	type = {Article},
	abstract = {Stable isotope incorporation studies with [1,2-C-13(2)]acetate, [1,2-C-13(2),O-18(1)]acetate, [1,2-C-13],mevalonolactone, and [2-C-13]mevalonolactone have been used to investigate the biosynthesis of the terpenoids albicanyl acetate (1), cadlinaldehyde (2), and luteone (3) by the dorid nudibranch Cadlina luteomarginata. The results have shown that all three terpenoids are synthesized de novo by C, luteomarginata and the incorporation patterns are consistent with the biogenetic proposal that the new cadlinalane and luteane carbon skeletons are formed by degradation of a sesterterpenoid precursor. This represents the first demonstration of sesterterpenoid biosynthesis by a marine mollusc. Quantitative analysis has shown that only a small turnover of metabolites takes place during the feeding experiments but that the newly formed molecules have extremely high levels of incorporation of labeled precursors.},
	keywords = {CARBON SKELETON, CHEMICAL DEFENSE, MARINE NATURAL-PRODUCTS, SPONGE APLYSILLA-GLACIALIS},
	isbn = {0022-3263},
	url = {<Go to ISI>://A1997YC65700039},
	author = {Kubanek, J. and Graziani, E. I. and Andersen, R. J.}
}
@article {7082,
	title = {CHROMODORANE DITERPENES FROM THE TROPICAL DORID NUDIBRANCH CHROMODORIS-CAVAE},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {69},
	number = {5},
	year = {1991},
	note = {ISI Document Delivery No.: FP799Times Cited: 9Cited Reference Count: 10},
	month = {May},
	pages = {768-771},
	type = {Article},
	abstract = {Two novel diterpenoids, chromodorolides A (1) and B (2), have been isolated from skin extracts of the tropical dorid nudibranch Chromodoris cavae. Complete NMR assignments are presented for chromodorolide A (1). The structure of chromodorolide B (2) has been solved by spectroscopic analysis. Chromodorolides A (1) and B (2) are the first examples of diterpenoids with the highly rearranged chromodorane carbon skeleton.},
	keywords = {CARBON SKELETON, CHROMODORANE, CHROMODORIS, DITERPENE, nudibranch},
	isbn = {0008-4042},
	url = {<Go to ISI>://A1991FP79900002},
	author = {Morris, S. A. and De Silva, E. D. and Andersen, R. J.}
}
@article {7120,
	title = {TERPENOIDS FROM THE SPONGE APLYSILLA-GLACIALIS AND SPECIMENS OF THE NUDIBRANCH CADLINA-LUTEOMARGINTA FOUND ON THE SPONGE},
	journal = {Journal of Organic Chemistry},
	volume = {56},
	number = {1},
	year = {1991},
	note = {ISI Document Delivery No.: EQ979Times Cited: 21Cited Reference Count: 27},
	month = {Jan},
	pages = {42-47},
	type = {Article},
	abstract = {Four new rearranged and/or degraded {\textquoteright}{\textquoteright}spongian{\textquoteright}{\textquoteright} terpenoids and one new {\textquoteright}{\textquoteright}marginatane{\textquoteright}{\textquoteright} diterpenoid have been isolated from the marine sponge Aplysilla glacialis. The structure of cadlinolide A (3) was solved by X-ray diffraction analysis, and the structures of cadlinolide B (4), aplysillolide A (5), aplysillolide B (6), and marginatone (7) were determined by extensive spectroscopic analysis and chemical interconversions. Glaciolide (2), cadlinolide A (3), and tetrahydroaplysulphurin-1 (8) were isolated from skin extracts of specimens of the dorid nudibranch Cadlina luteomarginata found feeding on A. glacialis.},
	keywords = {AMBLIOFURAN, CARBON SKELETON, CHROMODORIS-NORRISI, CONSTITUENTS, CYCLIZATION, DENDROCERATIDA, diterpenes, MARINE SPONGES, METABOLITES, OFFICINALIS},
	isbn = {0022-3263},
	url = {<Go to ISI>://A1991EQ97900010},
	author = {Tischler, M. and Andersen, R. J. and Choudhary, M. I. and Clardy, J.}
}
