Total synthesis of (±)-herbertenediol
作者： A. Srikrishna , G. Satyanarayana
DOI: 10.1016/J.TET.2006.01.021
关键词:
摘要: Abstract A formal total synthesis of the sesquiterpene (±)-herbertenediol and its dimers mastigophorenes A–D has been accomplished, starting from vanillin via 2,3-dimethoxy-5-methylbenzaldehyde. combination Claisen rearrangement ring-closing metathesis reactions were employed for generation two vicinal quaternary carbons on a cyclopentane ring.
elsevier.com
sci-hub.se 参考文章(51)
Gerhard Bringmann, Thomas Pabst, Petra Henschel, Jürgen Kraus, Karl Peters, Eva-Maria Peters, David S. Rycroft, Joseph D. Connolly, Nondynamic and Dynamic Kinetic Resolution of Lactones with Stereogenic Centers and Axes: Stereoselective Total Synthesis of Herbertenediol and Mastigophorenes A and B† Journal of the American Chemical Society. ,vol. 122, pp. 9127- 9133 ,(2000) , 10.1021/JA001455R
Yoshinori Asakawa, Reiko Matsuda, W.B. Schofield, S. Rob Gradstein, Cuparane- and isocuparane-type sesquiterpenoids in liverworts of the genus Herbertus Phytochemistry. ,vol. 21, pp. 2471- 2473 ,(1982) , 10.1016/0031-9422(82)85243-6
Emile Al-Farhan, Olusegun M. Falana, Philip M. Keehn, Robert Stevenson, A simple synthesis of cyclotribromoveratrylene (CTBV) : an extractive of the red alga Halopytis pinastroides Tetrahedron Letters. ,vol. 33, pp. 5885- 5886 ,(1992) , 10.1016/S0040-4039(00)61079-1
Akihiko Matsuo, Shunji Yuki, Mitsuru Nakayama, (−)-HERBERTENEDIOL AND (−)-HERBERTENOLIDE, TWO NEW SESQUITERPENOIDS OF THE ENT-HERBERTANE CLASS FROM THE LIVERWORT HERBERTA ADUNCA Chemistry Letters. ,vol. 12, pp. 1041- 1042 ,(1983) , 10.1246/CL.1983.1041
Joseph S. Byck, Charles R. Dawson, Synthesis of compounds structurally related to poison ivy urushiol. II. 4-Methyl-, 5-methyl-, 6-methyl-, and 4,5,6-trimethyl-3-pentadecylcatechol Journal of Organic Chemistry. ,vol. 33, pp. 2451- 2456 ,(1968) , 10.1021/JO01270A061
Hiroshi Irita, Toshihiro Hashimoto, Yoshiyasu Fukuyama, Yoshinori Asakawa, Herbertane-type sesquiterpenoids from the liverwort Herbertus sakuraii Phytochemistry. ,vol. 55, pp. 247- 253 ,(2000) , 10.1016/S0031-9422(00)00317-4
Hildegard Feld, Josef Zapp, Hans Becker, Secondary metabolites from the liverwort Tylimanthus renifolius. Phytochemistry. ,vol. 64, pp. 1335- 1340 ,(2003) , 10.1016/J.PHYTOCHEM.2003.08.021
Masao Toyota, Mutsumi Konoshima, Fumihiro Nagashima, Shizu Hirata, Yoshinori Asakawa, Butenolides from Marchantia paleacea subspecies diptera Phytochemistry. ,vol. 46, pp. 293- 296 ,(1997) , 10.1016/S0031-9422(97)00273-2
G. Buchi, B. Egger, New synthesis of cyclopentenones. Methyl jasmonate and jasmone Journal of Organic Chemistry. ,vol. 36, pp. 2021- 2023 ,(1971) , 10.1021/JO00813A045
William Summer. Johnson, Lucius. Werthemann, William R. Bartlett, Timothy J. Brocksom, Tsung-Tee. Li, D. John. Faulkner, Michael R. Petersen, Simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene Journal of the American Chemical Society. ,vol. 92, pp. 741- 743 ,(1970) , 10.1021/JA00706A074