Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(3): 431-436
DOI: 10.1055/s-0029-1217144
DOI: 10.1055/s-0029-1217144
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
The Stereoselective Total Synthesis of Aculeatin A and B via Prins Cyclization
Further Information
Received
26 August 2009
Publication Date:
27 November 2009 (online)
Publication History
Publication Date:
27 November 2009 (online)
Abstract
The total synthesis of aculeatins A and B is described proving the versatility of Prins cyclization in natural product synthesis. The approach is convergent and highly stereoselective. Morpholine amide coupling with an alkyne and PIFA-mediated oxidative spirocyclization were utilized as key steps.
Key words
aculeatins - Prins cyclization - morpholine amide - PIFA-mediated oxidative spirocyclization
-
1a
Heilmann J.Mayr S.Brun R.Rali T.Sticher O. Helv. Chim. Acta 2000, 83: 2939 -
1b
Heilmann J.Brun R.Mayr S.Rali T.Sticher O. Phytochemistry 2001, 57: 1281 -
2a
Chin Y.Salim AA.Su B.Mi Q.Chai H.Riswan SK.Leonardus BS.Ruskandi A.Farnsworth NR.Swanson SM.Kinghorn AD. J. Nat. Prod. 2008, 71: 390 -
2b
Peuchmaur M.Saïdani N.Botte C.Marechal E.Vial H.Wong DY. J. Med. Chem. 2008, 51: 4870 -
3a
Wong YS. Chem. Commun. 2002, 686 -
3b
Falomir E.Alvarez-Bercedo P.Carda M.Marco JA. Tetrahedron Lett. 2005, 46: 8407 -
3c
Baldwin JE.Adlington RM.Sham VWW.Marquez R.Bulger PG. Tetrahedron 2005, 61: 2353 -
3d
Alvarez-Bercedo P.Falomir E.Carda M.Marco JA. Tetrahedron 2006, 62: 9641 -
3e
Euchmaur M.Wong YS. J. Org. Chem. 2007, 72: 5374 -
3f
Chandrasekhar S.Rambabu C.Shyamsunder T. Tetrahedron Lett. 2007, 48: 4683 -
3g
Ramana CV.Srinivas B. J. Org. Chem. 2008, 73: 3915 -
3h
Zhen Z.Gao J.Wu S. J. Org. Chem. 2008, 73: 7310 -
3i
Suresh V.Selvam J.Rajesh K.Venkateswarlu Y. Tetrahedron: Asymmetry 2008, 19: 1509 - For the Prins cyclization, see for example:
-
4a
Barry CStJ.Crosby SR.Harding JR.Hughes RA.King CD.Parker GD.Willis CL. Org. Lett. 2003, 5: 2429 -
4b
Yang X.-F.Mague JT.Li C.-J. J. Org. Chem. 2001, 66: 739 -
4c
Aubele DL.Wan S.Floreancig PE. Angew. Chem. Int. Ed. 2005, 44: 3485 -
4d
Barry CS.Bushby N.Harding JR.Willis CS. Org. Lett. 2005, 7: 2683 -
4e
Cossey KN.Funk RL. J. Am. Chem. Soc. 2004, 126: 12216 -
4f
Crosby SR.Harding JR.King CD.Parker GD.Willis CL. Org. Lett. 2002, 4: 3407 -
4g
Marumoto S.Jaber JJ.Vitale JP.Rychnovsky SD. Org. Lett. 2002, 4: 3919 -
4h
Kozmin SA. Org. Lett. 2001, 3: 755 -
4i
Jaber JJ.Mitsui K.Rychnovsky SD. J. Org. Chem. 2001, 66: 4679 -
4j
Kopecky DJ.Rychnovsky SD. J. Am. Chem. Soc. 2001, 123: 8420 -
4k
Rychnovsky SD.Thomas CR. Org. Lett. 2000, 2: 1217 -
4l
Rychnovsky SD.Yang G.Hu Y.Khire UR. J. Org. Chem. 1997, 62: 3022 -
4m
Su Q.Panek JS. J. Am. Chem. Soc. 2004, 126: 2425 -
4n
Yadav JS.Reddy BVS.Sekhar KC.Gunasekar D. Synthesis 2001, 885 -
4o
Yadav JS.Reddy BVS.Reddy MS.Niranjan N. J. Mol. Catal. A: Chem. 2004, 210: 99 -
4p
Yadav JS.Reddy BVS.Reddy MS.Niranjan N.Prasad AR. Eur. J. Org. Chem. 2003, 1779 -
5a
Yadav JS.Reddy MS.Rao PP.Prasad AR. Tetrahedron Lett. 2006, 47: 4397 -
5b
Yadav JS.Reddy MS.Prasad AR. Tetrahedron Lett. 2006, 47: 4937 -
5c
Yadav JS.Reddy MS.Prasad AR. Tetrahedron Lett. 2005, 46: 2133 -
5d
Yadav JS.Reddy MS.Prasad AR. Tetrahedron Lett. 2006, 47: 4995 -
5e
Yadav JS.Reddy MS.Rao PP.Prasad AR. Synlett 2007, 2049 -
5f
Yadav JS.Rao PP.Reddy MS.Rao NV.Prasad AR. Tetrahedron Lett. 2007, 48: 1469 -
5g
Yadav JS.Kumar NN.Reddy MS.Prasad AR. Tetrahedron 2006, 63: 2689 -
5h
Rao AVR.Reddy ER.Joshi BV.Yadav JS. Tetrahedron Lett. 1987, 28: 6497 -
5i
Yadav JS.Sridhar Reddy M.Rao PP.Prasad AR. Synlett 2049, 2007 -
5j
Yadav JS.Issana A.Gayathri KU.Rao NV.Prasad AR. Synthesis 2008, 3945 - 6
Bonini C.Chiummiento L.Lopardo MT.Pullex M.Colobert F.Solladie G. Tetrahedron Lett. 2003, 44: 2695 -
7a
Yadav JS.Thrimurtulu N.Gayathri UK.Subba Reddy BV.Prasad AR. Tetrahedron Lett. 2008, 49: 6617 -
7b
Yadav JS.Sridhar Reddy M.Purushothama Rao P.Prasad AR. Tetrahedron Lett. 2006, 47: 4397 - 8
Mitsunobu O. Synthesis 1981, 1 - 9
Raghavan S.Ramakrishna Reddy S. Tetrahedron Lett. 2004, 45: 5593 - 10
Furst M.Ruck-Braun K. Synlett 2002, 1991 - 11
Martin R.Romea P.Tey C.Urpi F.Vilarrasa J. Synlett 1997, 1414 - For a review on hypervalent iodine compounds, see:
-
12a
Zhadankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 - For more recent developments, see:
-
12b
Moriaty RM. J. Org. Chem. 2005, 70: 2893 -
12c
Wirth T. Angew. Chem. Int. Ed. 2005, 44: 3656 - For oxidation of phenolic compounds with hypervalent iodine reagents, see:
-
13a
Moriarty RM.Prakash O. Org. React. 2001, 57: 327 -
13b
Rodriguez S.Wipf P. Synthesis 2004, 767