Total synthesis of macquarimicins using an intramolecular Diels-Alder approach inspired by a biosynthetic pathway

Journal of the American Chemical Society

Volumn 126, Issue 36, 2004, Pages 11254-11267

  Munakata, Ryosuke ^a   Katakai, Hironori ^a   Ueki, Tatsuo ^a   Kurosaka, Jun ^a   Takao, Ken Ichi ^a   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GEOMETRY; MOLECULAR BIOLOGY; REACTION KINETICS; STEREOCHEMISTRY; SUBSTRATES;

INTRAMOLECULAR DIELS-ALDER (IMDA) REACTIONS; MACQUARIMICINS; PENTACYCLIC FRAMEWORKS;

BIOSYNTHESIS;

1,6,8 NONATRIENE; 9 EPICOCHLEAMYCIN A; 9 EPICOCHLEAMYCIN B; ANTINEOPLASTIC ANTIBIOTIC; EPICHLOROHYDRIN; ETHYL 4,5 (ISOPROPYLIDENE)DIOXY 2 PENTENOATE; INDAN DERIVATIVE; MACQUARIMICIN A; MACQUARIMICIN B; MACQUARIMICIN C; NATURAL PRODUCT; TETRAHYDROINDANE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; DIELS ALDER REACTION; DRUG SYNTHESIS; MICROMONOSPORA; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STILLE REACTION;

BIOMIMETICS; CYCLIZATION; MACROLIDES; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 4544332948     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048320w     Document Type: Article

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163. Burke and co-workers have reported a retro hetero IMDA/IMDA reaction in an attempted Claisen rearrangement: Burke, S. D.; Armistead, D. M.; Shankaran, K. Tetrahedron Lett. 1986, 27, 6295-6298.
164. (a) Kitaaawa, Y.; Itoh, A.; Hashimoto, S.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3864-3867.
165. (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1977, 99, 3867-3868.
166. (c) Trost, B. M.; Ohmori, M.; Boyd, S. A.; Okawara, H.; Brickner, S. J. J. Am. Chem. Soc. 1989, 111, 8281-8284.
167. (d) Review: Trost, B. M. Anvew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192.
168. For recent applications, see: (a) Reference 21.
169. (b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 720, 2817-2825.
170. (c) Hoffmann, H. M. R.; Pohlmann, J. Tetrahedron Lett. 1998, 39, 7085-7088.
171. (d) Fürstner, A.; Krause, H. J. Org. Chem. 1999, 64, 8281-8286.
172. (e) Yuasa, H.; Makado, G.; Fukuyama, Y. Tetrahedron Lett. 2003, 44, 6235-6239.
173. 4, dppe, BSA, THF, reflux). However, the yield was capricious (51-86%) due to the formation of a terminal diene, which was formed via the β-hydride elimination of the intermediary π-allylpalladium complex. For the use of carbonates in Pd-catalyzed allylic alkylation, see: Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523-1529.
174. In the selenenylation reaction, addition of PhSeCl as a toluene solution, not a THF solution, was essential for maintaining reproducibility.
175. Although the intermediary selenide was a diastereomeric mixture (ca. 2:1), virtually one geometrical isomer was formed through the oxidation/syn-elimination process.
176. We explored the synthesis of 16 from the aforementioned linear α,β-unsaturated aldehyde 14 in a more straightforward manner by employing the intramolecular Knoevenagel reaction. However, the desired 17-membered carbocycle was not obtained despite extensive exploration.
177. In addition to 16 and 49, we also examined a TADA substrate without protecting groups for the 1,3-diol moiety. However, the TADA substrate in this case decomposed under the thermal conditions (150°C).
178. Under acidic conditions, the desired δ-lactone was not obtained; however, β-elimination of the C(16)-OH occurred to form a (Z)-α,β-unsaturated ketone substructure.
179. We also investigated the synthesis of 17 through a macroallylation strategy applied to an allyl acetate or carbonate bearing the preexisting β-keto-δ-lactone ring, but the yield of the macroallylation product was lower (ca. 30%) as compared to that obtained from the corresponding β3-ketoestet derivative 47a (84%).
180. The deprotection, proceeding in 64% yield, accompanied the formation of a dithioacetal.
181. 2/lutidine).
182. The α,β-unsaturated ketone might be produced by sequential β-elimination and decarboxylation as shown below.
183. As shown in Figure 7, irradiations at H(3) and H(14) led to the enhancement of the signals of H(14) and H(17a), respectively. These results indicate that the three hydrogen atoms are located on the same side of the 10-membered ring. Therefore, the C(2)-C(3) geometry was determined to be Z.
184. For examples of hetero Diels-Alder reactions using 2-methoxypropene as a dienophile, see: (a) Sato, M.; Kano, K.; Kitazawa, N.; Hisamichi, H.; Kaneko, C. Heterocycles 1990, 31, 1229-1232.
185. (b) Cravotto, G.; Nano, G. M.; Palmisano, G.; Tagliapietra, S. Tetrahedron: Asymmetry 2001, 12, 707-709.
186. (c) Nair, V.; Tressa, P. M. Tetrahedron Lett. 2001, 42, 4549-4551.
187. 2 led to complex mixtures.