P.L. wishes to acknowledge support by the Alexander von Humboldt foundation.
Communication
You have free access to this content
Total Synthesis of (+)-Lactiflorin by an Intramolecular [2+2] Photocycloaddition†
Article first published online: 21 DEC 2011
DOI: 10.1002/anie.201106889
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Lu, P. and Bach, T. (2012), Total Synthesis of (+)-Lactiflorin by an Intramolecular [2+2] Photocycloaddition. Angew. Chem. Int. Ed., 51: 1261–1264. doi: 10.1002/anie.201106889
- †
Publication History
- Issue published online: 24 JAN 2012
- Article first published online: 21 DEC 2011
- Manuscript Revised: 24 OCT 2011
- Manuscript Received: 28 SEP 2011
Funded by
- Alexander von Humboldt foundation
- 1Review: , , Angew. Chem. 2005, 117, 1036–1069;Angew. Chem. Int. Ed. 2005, 44, 1012–1044.Direct Link:Direct Link:
- 2Selected recent examples:
- 2a, , , , , , , Angew. Chem. 2011, 123, 318–323;Angew. Chem. Int. Ed. 2011, 50, 304–309;Direct Link:Direct Link:
- 2b, , , , , , Angew. Chem. 2010, 122, 764–768; Angew. Chem. Int. Ed. 2010, 49, 752–756;
- 2c, , , Angew. Chem. 2010, 122, 9415–9418;Angew. Chem. Int. Ed. 2010, 49, 9229–9232;Direct Link:Direct Link:
- 2d, , , , , , , , , J. Am. Chem. Soc. 2010, 132, 7138–7152;
- 2e
- 2f
- 2g, , Angew. Chem. 2009, 121, 4262–4265;Angew. Chem. Int. Ed. 2009, 48, 4198–4201.Direct Link:Direct Link:
- 3
- 4
- 5
- 6Isolation:
- 6a
- 6b
- 7Previous syntheses:
- 7a
- 7b
- 8Reviews:
- 8a, , in Handbook of Synthetic Photochemistry (Eds.: A. Albini, M. Fagnoni), Wiley-VCH, Weinheim, 2009, pp. 171–215;
- 8bin CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2004, pp. 71/1–71/14;
- 8c
- 8d
- 8e
- 9For photochemical key steps in natural product synthesis, see:
- 9a
- 9b
- 9c, , Angew. Chem. 2011, 123, 1032–1077;Angew. Chem. Int. Ed. 2011, 50, 1000–1045.Direct Link:Direct Link:
- 10For a previous approach related to the tricyclic core of structure 3, see: , , , J. Org. Chem. 2003, 68, 1994–1997.
- 11
- 11a, , Angew. Chem. 2008, 120, 5160–5162;Angew. Chem. Int. Ed. 2008, 47, 5082–5084;Direct Link:Direct Link:
- 11b
- 11c
- 12For further details, see Part B of the Supporting Information.
- 13
- 13a
- 13b
- 14
- 15For a closely related example, see: , , Chem. Eur. J. 2009, 15, 58–62.Direct Link:
- 16
- 17
- 18For a recent study on the regioselectivity of the related intramolecular [2+2] photocycloaddition of tetronates, see: , , , J. Org. Chem. 2011, 76, 5924–5935.
- 19, , , Handbook of Photochemistry, 2nd ed., Marcel Dekker, New York, 1993.
- 20For further details concerning the glucosylation step, see Part C of the Supporting Information.
- 21For the synthesis of the glucosyl donor precursor, see: , , Org. Lett. 2009, 11, 1305–1307.
- 22
- 22a
- 22b
- 22cFor a recent review of PTFAI-based glycosyl donors, see: , , Chem. Commun. 2010, 46, 4668–4679.
- 23, , , Angew. Chem. 2008, 120, 4411–4414;Angew. Chem. Int. Ed. 2008, 47, 4339–4342.Direct Link:Direct Link:
- 24For related cases, in which α-glycosylation was a significant side reaction with sterically hindered alcohols, see:
- 24a, , Angew. Chem. 1991, 103, 179–182;Angew. Chem. Int. Ed. Engl. 1991, 30, 180–183;Direct Link:Direct Link:
- 24b
- 24c, , , Carbohydr. Res. 2003, 338, 307–311; , , , , , Carbohydr. Res. 2006, 341, 1312–1321.

1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
